Dicyclohexylcarbodiimide → HCID 178445956, compound

HRID 616485Notes

Reaction equation

HRID 616485 reaction equation
[NH2:1][C@H:2]([C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].CC1C=CC(S(O)(=O)=O)=CC=1.C(N1CCOCC1)C.CN(C=O)C.[NH:41]([C:99]([O:101][CH2:102][C:103]1[CH:108]=[CH:107][CH:106]=[CH:105][CH:104]=1)=[O:100])[CH2:42][CH2:43][C:44]([NH:46][C@H:47]([C:58]([NH:60][CH2:61][C:62]([NH:64][C@H:65]([C:73]([NH:75][C@H:76]([C:84]([NH:86][C@H:87]([C:96](O)=[O:97])[CH2:88][C:89]1[CH:94]=[CH:93][C:92]([OH:95])=[CH:91][CH:90]=1)=[O:85])[CH2:77][C:78]1[CH:83]=[CH:82][CH:81]=[CH:80][CH:79]=1)=[O:74])[CH2:66][C:67]1[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=1)=[O:63])=[O:59])[CH2:48][CH2:49][CH2:50][NH:51][C:52](=[NH:57])[NH:53][N+:54]([O-:56])=[O:55])=[O:45].C1C2C3C(=O)N(O)C(=O)C3C1C=C2.C1CCC(N=C=NC2CCCCC2)CC1>CN(C=O)C>[NH:41]([C:99]([O:101][CH2:102][C:103]1[CH:104]=[CH:105][CH:106]=[CH:107][CH:108]=1)=[O:100])[CH2:42][CH2:43][C:44]([NH:46][C@H:47]([C:58]([NH:60][CH2:61][C:62]([NH:64][C@H:65]([C:73]([NH:75][C@H:76]([C:84]([NH:86][C@H:87]([C:96]([NH:1][C@H:2]([C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5])=[O:97])[CH2:88][C:89]1[CH:90]=[CH:91][C:92]([OH:95])=[CH:93][CH:94]=1)=[O:85])[CH2:77][C:78]1[CH:79]=[CH:80][CH:81]=[CH:82][CH:83]=1)=[O:74])[CH2:66][C:67]1[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=1)=[O:63])=[O:59])[CH2:48][CH2:49][CH2:50][NH:51][C:52](=[NH:57])[NH:53][N+:54]([O-:56])=[O:55])=[O:45]

Participants

7

Reactant 5

HCID 10868DicyclohexylcarbodiimideHCID 895293a,4,7,7a-Tetrahydro-2-hydroxy-4,7-methano-1H-isoindole-1,3(2H)-dioneHCID 6451312L-Leucine, phenylmethyl ester, 4-methylbenzenesulfonate (1:1)HCID 131710603HCID 131710603, compoundHCID 178512168HCID 178512168, compound

Product 1

HCID 178445956HCID 178445956, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
-10 °C

Procedure

In 5 ml. of DMF was dissolved 275 mg. of H-Leu-OBzl-p-toluenesulfonate and the solution was neutralized with 0.9 ml. of 10 % N-ethylmorpholine-DMF. Under cooling at -10° C, 670 mg. of Z-β-Ala-Arg(NO2)-Gly-Phe-Phe-Tyr-OH, 251 mg. of HONB and 289 mg. of DCC were added. The mixture was stirred for 12 hours and the formed DC-urea was filtered off. The DMF was distilled off under reduced pressure and 30 ml. of water was added to the residue. The resulting precipitate was collected by filtration, washed with hot methanol and dried. Yield 703 mg. (87.9 %) melting point: 178- 181° C; α!D23 -15.0°(c=1.02 %, DMF)

Workup

  1. filtrationthe formed DC-urea was filtered off
  2. distillationThe DMF was distilled off under reduced pressure and 30 ml
  3. additionof water was added to the residue
  4. filtrationThe resulting precipitate was collected by filtration
  5. washwashed with hot methanol
  6. customdried
  7. customα!D23 -15.0°(c=1.02 %, DMF)

Sources & evidence

ORD record
ord-9513be9ed3db40c3ad219404962f9d2e
Source dataset
uspto-grants-1978_02
Patent number
US04073890

Reaction notes

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