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

HRID 2230215Notes

Reaction equation

HRID 2230215 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>[NH2:25][CH2:24][C@H:16]([NH:15][C:13]([O:12][CH2:11][C:1]12[CH2:8][CH:7]3[CH2:6][CH:5]([CH2:4][CH:3]([CH2:9]3)[CH2:2]1)[CH2:10]2)=[O:14])[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18]

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-adamantylmethyloxycarbonylamino)-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 dichloromethane phases were then dried over sodium sulfate. After filtration and removal of the solvent in vacuo, 6.35 g (94%) of tert-butyl (S)-3-amino-2-(1-adamantylmethyloxycarbonylamino)propionate were obtained as a colorless solid.

Workup

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

Sources & evidence

ORD record
ord-ef94e7f3396c4ff9b3c5fb97c13cac94
Source dataset
uspto-grants-2002_07
Patent number
US06423712B1

Reaction notes

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