2-tert-Butoxycarbonylamino-3-(4-nitro-phenyl)-propionic acid → HCID 22828229, compound

HRID 1633311Notes

Reaction equation

[NH2:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[C@@H:11]1[O:16][C@H:15]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C@@H:14]([NH2:22])[C@H:12]1[OH:13].[C:23]([O:27][C:28]([NH:30][CH:31]([C:42](O)=[O:43])[CH2:32][C:33]1[CH:38]=[CH:37][C:36]([N+:39]([O-:41])=[O:40])=[CH:35][CH:34]=1)=[O:29])([CH3:26])([CH3:25])[CH3:24]>>[NH2:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[C@@H:11]1[O:16][C@H:15]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C@@H:14]([NH:22][C:42](=[O:43])[CH:31]([CH2:32][C:33]2[CH:34]=[CH:35][C:36]([N+:39]([O-:41])=[O:40])=[CH:37][CH:38]=2)[NH:30][C:28]([O:27][C:23]([CH3:26])([CH3:24])[CH3:25])=[O:29])[C@H:12]1[OH:13]

Participants

Reactant 2

HCID 1180712-tert-Butoxycarbonylamino-3-(4-nitro-phenyl)-propionic acid

HCID 54364747HCID 54364747, compound

Product 1

HCID 22828229HCID 22828229, compoundYield 46.7%

Procedure

Ethyl 1-(6-amino-9H-purin-9-yl)-1,3-dideoxy-3-[N-tert-butoxycarbonyl-β-(4-nitrophenyl)-D,L-alanylamino]-β-D-ribofuranuronate (280 mg) was prepared by reacting ethyl 1-(6-amino-9H-purin-9-yl)-1,3-dideoxy-3-amino-β-D-ribofuranuronate (308 mg) prepared in Example 63 with N-tert-butoxycarbonyl-β-(4-nitrophenyl)-D,L-alanine (310 mg) according to a similar manner to that of Example 64, mp. 170°-180° C. (dec.).

Sources & evidence

ORD record: ord-f363c474cc274046918c1051aa8672fa
Source dataset: uspto-grants-1984_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04479942

Reaction notes

Loading…