Dicyclohexylcarbodiimide → tertiary butyloxycarbonylglycyl-epsilon-benzyloxycarbonyl-L-lysyl-sarcosyl-L-proline methyl ester

HRID 979448Notes

Reaction equation

HRID 979448 reaction equation
C1(NC2CCCCC2)CCCCC1.[C:14]([O:18][C:19]([NH:21][CH2:22][C:23]([OH:25])=O)=[O:20])([CH3:17])([CH3:16])[CH3:15].Cl.[CH3:27][O:28][C:29](=[O:59])[C@@H:30]1[CH2:34][CH2:33][CH2:32][N:31]1[C:35](=[O:58])[CH2:36][N:37]([C:39](=[O:57])[C@H:40]([CH2:42][CH2:43][CH2:44][CH:45]([C:47]([O:49][CH2:50][C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)=[O:48])[NH2:46])[NH2:41])[CH3:38].C1(N=C=NC2CCCCC2)CCCCC1.COC(=O)[C@@H]1CCCN1C(=O)CN(C(=O)[C@](C(OC(C)(C)C)=O)(CCCC(C(OCC1C=CC=CC=1)=O)N)N)C>C(Cl)(Cl)Cl>[CH3:27][O:28][C:29](=[O:59])[C@@H:30]1[CH2:34][CH2:33][CH2:32][N:31]1[C:35](=[O:58])[CH2:36][N:37]([C:39](=[O:57])[C@H:40]([CH2:42][CH2:43][CH2:44][CH:45]([C:47]([O:49][CH2:50][C:51]1[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=1)=[O:48])[NH2:46])[NH:41][C:23](=[O:25])[CH2:22][NH:21][C:19]([O:18][C:14]([CH3:15])([CH3:16])[CH3:17])=[O:20])[CH3:38]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 12453843t-Butyloxycarbonylglycine dicyclohexylamineHCID 70444626epsilon-benzyloxycarbonyl-L-lysyl-sarcosyl-L-proline methyl ester hydrochlorideHCID 86741546alpha-tertiary butyloxycarbonyl-epsilon-benzyloxycarbonyl-L-lysylsarcosyl-L-proline methyl ester

Product 1

HCID 86741545tertiary butyloxycarbonylglycyl-epsilon-benzyloxycarbonyl-L-lysyl-sarcosyl-L-proline methyl esterYield 73.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To 50 ml of a solution of 2.79 g (0.0078 mol) of tertiary butyloxycarbonylglycine dicyclohexylamine salt and 3.96 g (0.0078 mol) of ε-benzyloxycarbonyl-L-lysyl-sarcosyl-L-proline methyl ester hydrochloride in chloroform, 5 ml of a solution of 1.61 g (0.0078 mol) of dicyclohexylcarbodiimide in chloroform was added at -10° C. Thereafter, the resultant mixture was treated by the procedure followed in the preparation of α-tertiary butyloxycarbonyl-ε-benzyloxycarbonyl-L-lysylsarcosyl-L-proline methyl ester in (A) above including such step as stirring at -10° C. for five hours and at room temperature overnight, for example. Consequently, there was obtained 3.55 g (yield 73%) of tertiary butyloxycarbonylglycyl-ε-benzyloxycarbonyl-L-lysyl-sarcosyl-L-proline methyl ester in white solid form having a melting point of 52° to 54° C.

Workup

  1. customas stirring at -10° C. for five hours and at room temperature overnight, for example

Sources & evidence

ORD record
ord-efb3e66b032f4e9e90064bbeb1ef0cb1
Source dataset
uspto-grants-1987_05
Patent number
US04668397

Reaction notes

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