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1-Adamantyl fluoroformate → (S)-2-(Adamantan-1-yloxycarbonylamino)-3,3-dimethyl-butyric acid methyl ester

HRID 1365018
Notes
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Reaction equation

HRID 1365018 reaction equation
[NH2:1][C@@H:2]([C:7]([CH3:10])([CH3:9])[CH3:8])[C:3]([O:5][CH3:6])=[O:4].CCN(C(C)C)C(C)C.F[C:21]([O:23][C:24]12[CH2:33][CH:28]3[CH2:29][CH:30]([CH2:32][CH:26]([CH2:27]3)[CH2:25]1)[CH2:31]2)=[O:22]>C(Cl)Cl>[CH3:6][O:5][C:3](=[O:4])[C@@H:2]([NH:1][C:21]([O:23][C:24]12[CH2:33][CH:28]3[CH2:27][CH:26]([CH2:32][CH:30]([CH2:29]3)[CH2:31]1)[CH2:25]2)=[O:22])[C:7]([CH3:10])([CH3:9])[CH3:8]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 644331-Adamantyl fluoroformateHCID 81531DiisopropylethylamineHCID 11309583Methyl L-tert-leucinate

Product 1

HCID 57945074(S)-2-(Adamantan-1-yloxycarbonylamino)-3,3-dimethyl-butyric acid methyl esterYield 80.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of (S)-methyl 2-amino-3,3-dimethylbutanoate (200 mg, 1.377 mmol) and DIEA (0.481 mL, 2.75 mmol) in DCM (2 mL) solution was add 1-adamantyl fluoroformate (334 mg, 1.515 mmol). The reaction mixture was stirred at rt overnight. The compound was purified by silica gel column chromatography (20% EtOAc/80% hexane) to give a colorless oil (358 mg, 68%) as product.

Workup

  1. customThe compound was purified by silica gel column chromatography (20% EtOAc/80% hexane)

Sources & evidence

ORD record
ord-c3bca80dad564f57bef7756675048af5
Source dataset
uspto-grants-2011_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07888464B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes