Ethyl 2-isocyanato-2-methylpropanoate → 2(R)-[1(S)-(Hydroxycarbamoyl)-4-phenylbutyl]-4-methyl-N-(4,4-dimethyl-2,5-dioxo-1-imidazolidinyl)valeramide

HRID 651791Notes

Reaction equation

HRID 651791 reaction equation
O1CCCCC1[O:7][NH:8][C:9]([C@H:11]([C@@H:21]([CH2:34][CH:35]([CH3:37])[CH3:36])[C:22]([NH:24][N:25]1[C:29](=[O:30])[C:28]([CH3:32])([CH3:31])[NH:27][C:26]1=[O:33])=[O:23])[CH2:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:10].C(OC([C@H]([C@@H](CC(C)C)C(NN)=O)CCCC1C=CC=CC=1)=O)(C)(C)C.N(C(C)(C)C(OCC)=O)=C=O>>[OH:7][NH:8][C:9]([C@H:11]([C@@H:21]([CH2:34][CH:35]([CH3:37])[CH3:36])[C:22]([NH:24][N:25]1[C:29](=[O:30])[C:28]([CH3:32])([CH3:31])[NH:27][C:26]1=[O:33])=[O:23])[CH2:12][CH2:13][CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[O:10]

Participants

4

Reactant 3

HCID 21709191Ethyl 2-isocyanato-2-methylpropanoateHCID 702001082(R)-[1(S)-(tert-butoxycarbonyl)-4-phenylbutyl]-4-methylvalerohydrazideHCID 867573022(R)-[1(S)-[(tetrahydro-2(RS)-pyranyloxy)carbamoyl]-4-phenylbutyl]-4-methyl-N-(4,4-dimethyl-2,5-dioxo-1-imidazolidinyl)valeramide

Product 1

HCID 867573012(R)-[1(S)-(Hydroxycarbamoyl)-4-phenylbutyl]-4-methyl-N-(4,4-dimethyl-2,5-dioxo-1-imidazolidinyl)valeramide

Procedure

The 2(R)-[1(S)-[(tetrahydro-2(RS)-pyranyloxy)carbamoyl]-4-phenylbutyl]-4-methyl-N-(4,4-dimethyl-2,5-dioxo-1-imidazolidinyl)valeramide used as the starting material was prepared in a manner analogous to that described in Example 7, part (ii) and Example 1, parts (vii) and (viii), starting from 2(R)-[1(S)-(tert-butoxycarbonyl)-4-phenylbutyl]-4-methylvalerohydrazide and ethyl 2-isocyanato-2-methylpropionate.

Workup

  1. customwas prepared in a manner analogous to

Sources & evidence

ORD record
ord-a8a473d3449c42248e3be989a026b466
Source dataset
uspto-grants-2001_08
Patent number
US06281363B1

Reaction notes

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