Dimethylformamide → HCID 131711814, compound

HRID 2057848Notes

Reaction equation

HRID 2057848 reaction equation
C1CCC(N=C=N[CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)CC1.[NH2:16][C@H:17]([C:30]([NH:32][C@H:33]([C:39]([NH:41][C@H:42]([C:47]([NH:49][C@H:50]([C:60]([NH:62][C@H:63]([C:68]([NH:70][C@H:71]([C:84]([NH:86][C@H:87]([C:109]([NH:111][C@H:112]([C:117]([O:119][C:120]([CH3:123])([CH3:122])[CH3:121])=[O:118])[CH2:113][C:114](=[O:116])[NH2:115])=[O:110])[CH2:88][S:89][C:90]([C:103]1[CH:108]=[CH:107][CH:106]=[CH:105][CH:104]=1)([C:97]1[CH:102]=[CH:101][CH:100]=[CH:99][CH:98]=1)[C:91]1[CH:96]=[CH:95][CH:94]=[CH:93][CH:92]=1)=[O:85])[CH2:72][C:73]1[CH:78]=[CH:77][C:76]([O:79][C:80]([CH3:83])([CH3:82])[CH3:81])=[CH:75][CH:74]=1)=[O:69])[CH2:64][C:65](=[O:67])[NH2:66])=[O:61])[CH2:51][CH2:52][C:53](=[O:59])[O:54][C:55]([CH3:58])([CH3:57])[CH3:56])=[O:48])[CH2:43][CH:44]([CH3:46])[CH3:45])=[O:40])[CH2:34][CH2:35][C:36](=[O:38])[NH2:37])=[O:31])[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[CH:21][CH:20]=1.[NH:124]([C:172]([O:174][C:175](C1C=C(OC)C=C(OC)C=1)([CH3:177])[CH3:176])=[O:173])[C@H:125]([C:130]([NH:132][C@H:133]([C:155]([NH:157][C@H:158]([C:161]([NH:163][C@H:164]([C:169](O)=[O:170])[CH2:165][CH:166]([CH3:168])[CH3:167])=[O:162])[CH2:159][OH:160])=[O:156])[CH2:134][S:135][C:136]([C:149]1[CH:154]=[CH:153][CH:152]=[CH:151][CH:150]=1)([C:143]1[CH:148]=[CH:147][CH:146]=[CH:145][CH:144]=1)[C:137]1[CH:142]=[CH:141][CH:140]=[CH:139][CH:138]=1)=[O:131])[C@H:126]([CH2:128][CH3:129])[CH3:127].C1C=CC2N(O)N=NC=2C=1.C(N1C[CH2:204][O:203]CC1)C.CN(C)[CH:208]=[O:209]>O>[NH:124]([C:172]([O:174][C:175]([C:10]1[CH:11]=[C:12]([O:203][CH3:204])[CH:13]=[C:14]([O:209][CH3:208])[CH:15]=1)([CH3:177])[CH3:176])=[O:173])[C@H:125]([C:130]([NH:132][C@H:133]([C:155]([NH:157][C@H:158]([C:161]([NH:163][C@H:164]([C:169]([NH:16][C@H:17]([C:30]([NH:32][C@H:33]([C:39]([NH:41][C@H:42]([C:47]([NH:49][C@H:50]([C:60]([NH:62][C@H:63]([C:68]([NH:70][C@H:71]([C:84]([NH:86][C@H:87]([C:109]([NH:111][C@H:112]([C:117]([O:119][C:120]([CH3:121])([CH3:122])[CH3:123])=[O:118])[CH2:113][C:114](=[O:116])[NH2:115])=[O:110])[CH2:88][S:89][C:90]([C:91]1[CH:92]=[CH:93][CH:94]=[CH:95][CH:96]=1)([C:103]1[CH:104]=[CH:105][CH:106]=[CH:107][CH:108]=1)[C:97]1[CH:98]=[CH:99][CH:100]=[CH:101][CH:102]=1)=[O:85])[CH2:72][C:73]1[CH:78]=[CH:77][C:76]([O:79][C:80]([CH3:83])([CH3:82])[CH3:81])=[CH:75][CH:74]=1)=[O:69])[CH2:64][C:65](=[O:67])[NH2:66])=[O:61])[CH2:51][CH2:52][C:53](=[O:59])[O:54][C:55]([CH3:56])([CH3:57])[CH3:58])=[O:48])[CH2:43][CH:44]([CH3:46])[CH3:45])=[O:40])[CH2:34][CH2:35][C:36](=[O:38])[NH2:37])=[O:31])[CH2:18][C:19]1[CH:20]=[CH:21][C:22]([O:25][C:26]([CH3:27])([CH3:28])[CH3:29])=[CH:23][CH:24]=1)=[O:170])[CH2:165][CH:166]([CH3:167])[CH3:168])=[O:162])[CH2:159][OH:160])=[O:156])[CH2:134][S:135][C:136]([C:143]1[CH:144]=[CH:145][CH:146]=[CH:147][CH:148]=1)([C:149]1[CH:154]=[CH:153][CH:152]=[CH:151][CH:150]=1)[C:137]1[CH:142]=[CH:141][CH:140]=[CH:139][CH:138]=1)=[O:131])[C@H:126]([CH2:128][CH3:129])[CH3:127]

Participants

8

Reactant 6

HCID 6228DimethylformamideHCID 7525EthylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 131711815HCID 131711815, compoundHCID 131711816HCID 131711816, compound

Product 1

HCID 131711814HCID 131711814, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

3.4 g (16.4 mmoles) of DCCI are added at 0° C. to a solution of 22.8 g (14 mmoles) of H-Tyr(But)-Gln-Leu-Glu(OBut)-Asn-Tyr(But)-Cys(Trt)-Asn-OBut, 14.1 g (15.4 mmoles) of Ddz-Ile-Cys(Trt)-Ser-Leu-OH.1 H2O, 2.08 g (15.4 mmoles) of HOBt and 1.8 ml (14 mmoles) of N-ethylmorpholine in 70 ml of dimethylformamide. The mixture is stirred for 1 hour at 0° C. and 3 hours at room temperature and is then left to stand overnight at room temperature, and the precipitate is filtered off. The filtrate is concentrated in vacuo and the residue is successively triturated with NaHCO3 solution, citrate buffer (pH 3), NaHCO3 solution and water and is filtered off in each case. It is dried over P2O5.

Workup

  1. waitis then left
  2. waitto stand overnight at room temperature
  3. filtrationthe precipitate is filtered off
  4. concentrationThe filtrate is concentrated in vacuo
  5. customthe residue is successively triturated with NaHCO3 solution, citrate buffer (pH 3), NaHCO3 solution and water
  6. filtrationis filtered off in each case
  7. dry with materialIt is dried over P2O5

Sources & evidence

ORD record
ord-5d0ca1f2c5544370bf70e5b6c8921bb5
Source dataset
uspto-grants-1980_07
Patent number
US04212796

Reaction notes

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