Methyl 1-amino-1-cyclopentanecarboxylate, HCl → 1-[(R)-2-bromo-3-methylbutanoylamino]cyclopentanecarboxylic acid

HRID 1836608Notes

Reaction equation

HRID 1836608 reaction equation
C(NC(C)C)(C)C.[Br:8][C@H:9]([CH:13]([CH3:15])[CH3:14])[C:10](O)=[O:11].Cl.C[O:18][C:19](=[O:26])[C:20]1([CH2:25][CH2:24][CH2:23][CH2:22]1)[NH2:21]>>[Br:8][C@H:9]([CH:13]([CH3:15])[CH3:14])[C:10]([NH:21][C:20]1([C:19]([OH:26])=[O:18])[CH2:25][CH2:24][CH2:23][CH2:22]1)=[O:11]

Participants

3

Reactant 2

HCID 11513856Methyl 1-amino-1-cyclopentanecarboxylate, HClHCID 56845281(r)-2-Bromoisovaleric acid diisopropylamine salt

Product 1

HCID 599024141-[(R)-2-bromo-3-methylbutanoylamino]cyclopentanecarboxylic acid

Procedure

The 1-[(R)-2-bromo-3-methylbutanoylamino]cyclopentanecarboxylic acid starting material is prepared essentially by methodology described in WO 99/55726 by condensation of (R)-2-bromo-3-methylbutanoic acid diisopropylamine salt (prepared from L-valine) with cycloleucine methyl ester hydrochloride.

Sources & evidence

ORD record
ord-2249e067b10c4a55af098f8f0f53c460
Source dataset
uspto-grants-2004_08
Patent number
US06777443B2

Reaction notes

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