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

HRID 1167678Notes

Reaction equation

HRID 1167678 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.C([O-])(O)=O.[Na+]>ClCCl.FC(F)(F)C(O)=O>[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

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 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 (13.10) in 180 ml of trifluoroacetic acid dichloromethane=1/1 is added, after 1 min, to 1.5 ml of an ice-cold solution of NaHCO3. The solution is extracted 3 times with dichloromethane and the dichloromethane phase is then dried over sodium sulfate. 6.35 g (94%) of (13.11) are obtained as a colorless solid after filtering and removing the solvent in vacuo.

Workup

  1. extractionThe solution is extracted 3 times with dichloromethane
  2. dry with materialthe dichloromethane phase is then dried over sodium sulfate

Sources & evidence

ORD record
ord-171ef436feab4d7484a2e34ad77755c0
Source dataset
uspto-grants-2003_09
Patent number
US06620820B2

Reaction notes

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