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

HRID 1883089Notes

Reaction equation

HRID 1883089 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-ad35b1ab9122434dbcffa77823c51a70
Source dataset
uspto-grants-2004_07
Patent number
US06759424B2

Reaction notes

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