Benzyl chloroformate → (2S)-2-{[(benzyloxy)carbonyl]amino}-2-(3-hydroxyadamantan-1-yl)acetic acid

HRID 1184046Notes

Reaction equation

HRID 1184046 reaction equation
Cl.[NH2:2][C@@H:3]([C:7]12[CH2:16][CH:11]3[CH2:12][CH:13]([CH2:15][C:9]([OH:17])([CH2:10]3)[CH2:8]1)[CH2:14]2)[C:4]([OH:6])=[O:5].[OH-].[Na+].Cl[C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22]>O>[CH2:24]([O:23][C:21]([NH:2][C@@H:3]([C:7]12[CH2:16][CH:11]3[CH2:12][CH:13]([CH2:15][C:9]([OH:17])([CH2:10]3)[CH2:8]1)[CH2:14]2)[C:4]([OH:6])=[O:5])=[O:22])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 14798Sodium HydroxideHCID 86703402(2S)-2-amino-2-(3-hydroxyadamantan-1-yl)acetic acid hydrochloride

Product 1

HCID 86703400(2S)-2-{[(benzyloxy)carbonyl]amino}-2-(3-hydroxyadamantan-1-yl)acetic acidYield 115.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The (2S)-2-amino-2-(3-hydroxyadamantan-1-yl)acetic acid hydrochloride (20 g) was dissolved in 100 ml water at 25-30° C. The pH of the solution was adjusted to 8.5-9.5 with aqueous sodium hydroxide solution at 5° C. To the mixture benzyl chloroformate (10.7 g) was added and set aside for 4 h at 25-30° C. The reaction mass was washed with MTBE (25 ml) and the pH of the aqueous phase adjusted to 2-3 with dilute hydrochloric acid. Aqueous phase was extracted with ethyl acetate, the organic phase dried and evaporated to yield 26 g (95%) of the title product. M.P 55-58° C., H1NMR (300 MHz, CDCl3): 1.39-1.58 (m, 12H), 2.04-2.07 (s, 2H), 3.86-3.89 (dd, 1H), 4.98 (s, 2H), 5.11 (s, 1H), 7.0 (d, 1H), 7.16-7.27 (m, 5H).

Workup

  1. washThe reaction mass was washed with MTBE (25 ml)
  2. extractionAqueous phase was extracted with ethyl acetate
  3. customthe organic phase dried
  4. customevaporated

Sources & evidence

ORD record
ord-cf66aa48c1144e52b1b54bc89eb64942
Source dataset
uspto-grants-2014_03
Patent number
US08664443B2

Reaction notes

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