Ethyl 1-isocyanatocyclobutane-1-carboxylate → 2(R)-[1(S)-(Hydroxycarbamoyl)-4-phenylbutyl]-4-methyl-N-(6,8-dioxo-5,7-diazaspiro[3,4]oct-7-yl)valeramide

HRID 651790Notes

Reaction equation

HRID 651790 reaction equation
C([O:8][NH:9][C:10]([C@H:12]([C@@H:22]([CH2:36][CH:37]([CH3:39])[CH3:38])[C:23]([NH:25][N:26]1[C:33](=[O:34])[C:29]2([CH2:32][CH2:31][CH2:30]2)[NH:28][C:27]1=[O:35])=[O:24])[CH2:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:11])C1C=CC=CC=1.C(OC([C@H]([C@@H](CC(C)C)C(NN)=O)CCCC1C=CC=CC=1)=O)(C)(C)C.N(C1(C(OCC)=O)CCC1)=C=O>>[OH:8][NH:9][C:10]([C@H:12]([C@@H:22]([CH2:36][CH:37]([CH3:39])[CH3:38])[C:23]([NH:25][N:26]1[C:33](=[O:34])[C:29]2([CH2:30][CH2:31][CH2:32]2)[NH:28][C:27]1=[O:35])=[O:24])[CH2:13][CH2:14][CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)=[O:11]

Participants

4

Reactant 3

HCID 13638278Ethyl 1-isocyanatocyclobutane-1-carboxylateHCID 702001082(R)-[1(S)-(tert-butoxycarbonyl)-4-phenylbutyl]-4-methylvalerohydrazideHCID 867573002(R)-[1(S)-(benzyloxycarbamoyl)-4-phenylbutyl]-4-methyl-N-(6,8-dioxo-5,7-diazaspiro[3.4]oct-7-yl)valeramide

Product 1

HCID 867572992(R)-[1(S)-(Hydroxycarbamoyl)-4-phenylbutyl]-4-methyl-N-(6,8-dioxo-5,7-diazaspiro[3,4]oct-7-yl)valeramide

Procedure

The 2(R)-[1(S)-(benzyloxycarbamoyl)-4-phenylbutyl]-4-methyl-N-(6,8-dioxo-5,7-diazaspiro[3.4]oct-7-yl)valeramide used as the starting material was prepared in a manner analogous to that described in Example 7, parts (ii) and (iii) starting from 2(R)-[1(S)-(tert-butoxycarbonyl)-4-phenylbutyl]-4-methylvalerohydrazide and ethyl 1-isocyanato-1-cyclobutane carboxylate.

Workup

  1. customwas prepared in a manner analogous to

Sources & evidence

ORD record
ord-1c3ad0ad08dd46d5ad88203428e50d7b
Source dataset
uspto-grants-2001_08
Patent number
US06281363B1

Reaction notes

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