tert-Butyl (2S)-(adamant-1-ylmethoxycarbonylamino)-3-tert-butoxycarbonylaminopropionate → tert-Butyl (2S)-(adamant-1-ylmethoxycarbonylamino)-3-aminopropionate

HRID 1636574Notes

Reaction equation

HRID 1636574 reaction equation
[C:1]12([CH2:11][O:12][C:13]([NH:15][C@@H:16]([CH2:24][NH:25]C(OC(C)(C)C)=O)[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[O:14])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2>FC(F)(F)C(O)=O.ClCCl>[C:1]12([CH2:11][O:12][C:13]([NH:15][C@@H:16]([CH2:24][NH2:25])[C:17]([O:19][C:20]([CH3:21])([CH3:22])[CH3:23])=[O:18])=[O:14])[CH2:10][CH:5]3[CH2:4][CH:3]([CH2:9][CH:7]([CH2:6]3)[CH2:8]1)[CH2:2]2

Participants

3

Reactant 1

HCID 68828668tert-Butyl (2S)-(adamant-1-ylmethoxycarbonylamino)-3-tert-butoxycarbonylaminopropionate

Product 1

HCID 53917304tert-Butyl (2S)-(adamant-1-ylmethoxycarbonylamino)-3-aminopropionateYield 94%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A solution of 8.7 g (19.22 mmol) of tert-butyl (S)-2-(1-adamantylmethyloxy-carbonylamino)-3-tert-butoxycarbonylamino-propionate in 180 ml of trifluoroacetic acid/dichloromethane (1:1) was added after 1 min to 1.5 l of ice-cold NaHCO3 solution, the mixture was extracted three times with dichloromethane and the combined dichloromethane phases were then dried over sodium sulfate. After filtration and removal of the solvent in vacuo, 6.35 g (94%) of the title compound were obtained as a colorless solid.

Workup

  1. extractionthe mixture was extracted three times with dichloromethane
  2. dry with materialthe combined dichloromethane phases were then dried over sodium sulfate
  3. filtrationAfter filtration and removal of the solvent in vacuo

Sources & evidence

ORD record
ord-ef6dbdf8297741e8a0698fcec6d546b9
Source dataset
uspto-grants-2000_03
Patent number
US06034238

Reaction notes

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