Carbodiimide → HCID 131714258, compound

HRID 370636Notes

Reaction equation

[NH:1]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C@H:2]([C:14]([OH:16])=O)[CH2:3][C:4](=[O:13])[O:5]CC1C=CC=CC=1.[NH2:24][C@H:25]([C:27]([NH:29][C@H:30]([C:32]([N:34]1[CH2:43][CH2:42][CH2:41][C@H:35]1[C:36]([NH:38][CH2:39][CH3:40])=[O:37])=[O:33])[CH3:31])=[O:28])[CH3:26].N=C=N>>[NH:1]([C:17]([O:19][C:20]([CH3:21])([CH3:22])[CH3:23])=[O:18])[C@H:2]([C:14]([NH:24][C@H:25]([C:27]([NH:29][C@H:30]([C:32]([N:34]1[CH2:43][CH2:42][CH2:41][C@H:35]1[C:36]([NH:38][CH2:39][CH3:40])=[O:37])=[O:33])[CH3:31])=[O:28])[CH3:26])=[O:16])[CH2:3][C:4](=[O:13])[OH:5]

Participants

Reactant 3

HCID 160435Carbodiimide

HCID 1581888N-tert-Butoxycarbonyl-L-aspartic acid beta-benzyl ester

HCID 13750002L-Alanyl-L-alanyl-N-ethyl-L-prolinamide

Product 1

HCID 131714258HCID 131714258, compoundYield 68%

Procedure

Condensation of BOC-Asp(OBzl) with Ala-Ala-Pro-NH-Et is achieved by the carbodiimide method as described in Example 1. Subsequent debenzylation by the procedure in Example 1 gives BOC-Asp-Ala-Ala-Pro-NH-Et in a yield of 68%; Rf =0.75(S)1. Acylation with undecanolylchloride, by the procedure in Example 3, produces the title product, Nα -Undecanoylaspartyl-alanyl-alanyl-proline ethylamide; m.p. 184°-189° C. (from water). Amino acid composition analysis yields; Asp 1.02, Pro 1.04, Ala 1.97.

Sources & evidence

ORD record: ord-85401f12751d4f70b3421421d534c1de
Source dataset: uspto-grants-1985_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04528133

Reaction notes

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