Dicyclohexylcarbodiimide → HCID 178455896, compound

HRID 1982312Notes

Reaction equation

HRID 1982312 reaction equation
[N:1]1([C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48])[CH2:46][CH2:45][CH2:44][C@H:2]1[C:3]([NH:5][C@H:6]([C:13]([N:15]1[CH2:43][CH2:42][CH2:41][C@H:16]1[C:17]([NH:19][C@H:20]([C:28]([NH:30][C@H:31]([C:38](O)=[O:39])[CH2:32][C:33]1[N:37]=[CH:36][NH:35][CH:34]=1)=[O:29])[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:18])=[O:14])[CH2:7][C:8]1[N:12]=[CH:11][NH:10][CH:9]=1)=[O:4].[NH2:54][C@H:55]([C@H:60]([CH2:62][C:63]([NH:65][C@H:66]([C:71]([NH:73][C@H:74]([C:81]([NH:83][C@H:84]([C:97]([O:99][CH3:100])=[O:98])[CH2:85][CH2:86][CH2:87][CH2:88][NH:89][C:90]([O:92][C:93]([CH3:96])([CH3:95])[CH3:94])=[O:91])=[O:82])[CH2:75][C:76]1[N:80]=[CH:79][NH:78][CH:77]=1)=[O:72])[C@H:67]([CH2:69][CH3:70])[CH3:68])=[O:64])[OH:61])[CH2:56][CH:57]([CH3:59])[CH3:58].C1C2C3C(=O)N(O)C(=O)C3C1C=C2.C1CCC(N=C=NC2CCCCC2)CC1>CN(C=O)C>[N:1]1([C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48])[CH2:46][CH2:45][CH2:44][C@H:2]1[C:3]([NH:5][C@H:6]([C:13]([N:15]1[CH2:43][CH2:42][CH2:41][C@H:16]1[C:17]([NH:19][C@H:20]([C:28]([NH:30][C@H:31]([C:38]([NH:54][C@H:55]([C@H:60]([CH2:62][C:63]([NH:65][C@H:66]([C:71]([NH:73][C@H:74]([C:81]([NH:83][C@H:84]([C:97]([O:99][CH3:100])=[O:98])[CH2:85][CH2:86][CH2:87][CH2:88][NH:89][C:90]([O:92][C:93]([CH3:96])([CH3:95])[CH3:94])=[O:91])=[O:82])[CH2:75][C:76]1[N:80]=[CH:79][NH:78][CH:77]=1)=[O:72])[C@H:67]([CH2:69][CH3:70])[CH3:68])=[O:64])[OH:61])[CH2:56][CH:57]([CH3:58])[CH3:59])=[O:39])[CH2:32][C:33]1[N:37]=[CH:36][NH:35][CH:34]=1)=[O:29])[CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)=[O:18])=[O:14])[CH2:7][C:8]1[N:12]=[CH:11][NH:10][CH:9]=1)=[O:4]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 895293a,4,7,7a-Tetrahydro-2-hydroxy-4,7-methano-1H-isoindole-1,3(2H)-dioneHCID 178451946HCID 178451946, compoundHCID 178455903HCID 178455903, compound

Product 1

HCID 178455896HCID 178455896, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

480 mg of Boc-Pro-His-Pro-Phe-His-OH (for manufacture see Example 1, stage 1.9), 340 mg of H-Sta-Ile-His-Lys(Boc)-OMe and 150 mg of HONB are dissolved, while heating, in 3.5 ml of DMF. After cooling to 0°, 170 mg of DCCI are added, whereupon stirring is carried out for 5 hours at 0° and the whole is left to stand at room temperature for 20 hours. The condensation product is precipitated by the addition of 35 ml of diisopropyl ether and filtered off. It is purified by Craig partitioning over 1000 stages in the same solvent system as described in stage 2.4 (K=0.6), yielding Boc-Pro-His-Pro-Phe-His-Sta-Ile-His-Lys(Boc)-OMe; Rf (A)=0.22; Rf (B)=0.21; Rf (E)=0.54.

Workup

  1. temperatureAfter cooling to 0°
  2. waitthe whole is left
  3. waitto stand at room temperature for 20 hours
  4. customThe condensation product is precipitated by the addition of 35 ml of diisopropyl ether
  5. filtrationfiltered off
  6. customIt is purified by Craig
  7. custompartitioning over 1000 stages in the same solvent system

Sources & evidence

ORD record
ord-f9fc76e9fd1d4c82addc793321b6312b
Source dataset
uspto-grants-1986_06
Patent number
US04595677

Reaction notes

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