Ammonia → N-[2-(N-Carbobenzoxy-4-O-benzyl-L-aspartyl-D-alanyl)-amino-2-deoxy-beta-D-glucopyranosyl]-N-dodecyl-dodecanamide

HRID 1636239Notes

Reaction equation

HRID 1636239 reaction equation
[NH2:1][C@@H:2]([C:4]([C@@H:6]1[C@@H:11]([OH:12])[C@H:10]([OH:13])[C@@H:9]([CH2:14][OH:15])[O:8][C@@:7]1([NH2:42])[N:16]([CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])[C:17](=[O:29])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[O:5])[CH3:3].[C:43]([NH:53][C@H:54]([C:66](O)=[O:67])[CH2:55][C:56]([O:58][CH2:59][C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1)=[O:57])([O:45][CH2:46][C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)=[O:44].N>ClCCl.CO>[C:43]([NH:53][C@H:54]([C:66]([NH:1][C@@H:2]([C:4]([C@@H:6]1[C@@H:11]([OH:12])[C@H:10]([OH:13])[C@@H:9]([CH2:14][OH:15])[O:8][C@@:7]1([NH2:42])[N:16]([CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])[C:17](=[O:29])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[O:5])[CH3:3])=[O:67])[CH2:55][C:56](=[O:57])[O:58][CH2:59][C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1)([O:45][CH2:46][C:47]1[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=1)=[O:44]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 476024-(Phenylmethyl) hydrogen N-((phenylmethoxy)carbonyl)-L-aspartateHCID 131721233N-(2D-alanyl-amino-2-deoxy-beta-D-glucopyranosyl)-N-dodecyl-dodecanamide

Product 1

HCID 131721715N-[2-(N-Carbobenzoxy-4-O-benzyl-L-aspartyl-D-alanyl)-amino-2-deoxy-beta-D-glucopyranosyl]-N-dodecyl-dodecanamideYield 63%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

from N-(2D-alanyl-amino-2-deoxy-β-D-glucopyranosyl)-N-dodecyl-dodecanamide and N-carbobenzoxy-4-O-benzyl-L-aspartic acid. Yield 63%. Rf 0.57 (dichloromethane/methanol/conc. ammonia 15:1:0.1).

Sources & evidence

ORD record
ord-cac57bc6e2ee42d4a931898e53ff28cb
Source dataset
uspto-grants-2000_03
Patent number
US06034055

Reaction notes

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