N-carbobenzyloxyalanine → HCID 178445951, compound

HRID 2309486Notes

Reaction equation

C([NH:11][CH2:12][C:13]([NH:15][C@H:16]([C:24]([NH:26][C@H:27]([C:32]([NH:34][C@H:35]([C:43]([OH:45])=[O:44])[CH2:36][CH2:37][CH2:38][NH:39][C:40](=[NH:42])[NH2:41])=[O:33])[CH2:28][CH:29]([CH3:31])[CH3:30])=[O:25])[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:14])(OCC1C=CC=CC=1)=O.[C:46]([NH:56][C@H:57]([C:59]([OH:61])=O)[CH3:58])([O:48][CH2:49][C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)=[O:47]>>[C:46]([NH:56][C@H:57]([C:59]([NH:11][CH2:12][C:13]([NH:15][C@H:16]([C:24]([NH:26][C@H:27]([C:32]([NH:34][C@H:35]([C:43]([OH:45])=[O:44])[CH2:36][CH2:37][CH2:38][NH:39][C:40](=[NH:41])[NH2:42])=[O:33])[CH2:28][CH:29]([CH3:31])[CH3:30])=[O:25])[CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)=[O:14])=[O:61])[CH3:58])([O:48][CH2:49][C:50]1[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=1)=[O:47]

Participants

Reactant 2

HCID 736104N-carbobenzyloxyalanine

HCID 178445952HCID 178445952, compound

Product 1

HCID 178445951HCID 178445951, compoundYield 79%

Procedure

From 0.63 g (1.01 mM) of carbobenzoxy-glycyl-phenylalanyl-leucyl-arginine and 0.38 g (1.11 mM) of p-nitrophenyl ester of carbobenzoxy-alanine, in a manner similar to that described hereinbefore, 0.56 g (79%) of carbobenzoxy-alanyl-glycyl-phenylalanyl-leucyl-arginine with m.p. of 147°-149° C. is obtained. [α]D25 =-4.0 (c 0.5, dimethylformamide). Rf1 =0.33 (C), Rf2 =0.35 (D), Rf3 =0.67 (chloroform:methanol: 32% acetic acid 60:45:20) (E).

Sources & evidence

ORD record: ord-388617ebce7c4d529408c2901b0156c5
Source dataset: uspto-grants-1987_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04695622

Reaction notes

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