Triethylamine → (S)-2-tert-Butoxycarbonylamino-5-(tert-butyl-diphenyl-silanyloxy)-pentanoic acid benzyl ester

HRID 1970488Notes

Reaction equation

HRID 1970488 reaction equation
[CH2:1]([O:8][C:9](=[O:23])[C@@H:10]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11][CH2:12][CH2:13][OH:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:24][C:25]([Si:28](Cl)([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)([CH3:27])[CH3:26].C(N(CC)CC)C>CN(C=O)C.CN(C1C=CN=CC=1)C>[CH2:1]([O:8][C:9](=[O:23])[C@@H:10]([NH:15][C:16]([O:18][C:19]([CH3:20])([CH3:22])[CH3:21])=[O:17])[CH2:11][CH2:12][CH2:13][O:14][Si:28]([C:25]([CH3:27])([CH3:26])[CH3:24])([C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 94078tert-ButyldiphenylchlorosilaneHCID 11056397(S)-Benzyl 2-((tert-butoxycarbonyl)amino)-5-hydroxypentanoate

Product 1

HCID 66854935(S)-2-tert-Butoxycarbonylamino-5-(tert-butyl-diphenyl-silanyloxy)-pentanoic acid benzyl ester

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2.5 g (S)-2-tert-Butoxycarbonylamino-5-hydroxy-pentanoic acid benzyl ester (prepared by adapting the procedure described by Diederichsen et al., Org. Biomol. Chem., 2005, 3, 1058) in 50 ml DMF were added 2.0 ml TBDPSCl, 1.2 ml triethylamine and 95 mg DMAP and the resulting suspension was stirred for 4 days. The solvent was evaporated, the residue dissolved in ethyl acetate and washed with aqueous LiCl (4 w/w), 0.1 M HCl and saturated NaHCO3. The crude product obtained after evaporation of the solvent was purified by chromatography on silica using heptane/ethyl acetate 12/1 as eluent. Yield: 2.0 g colorless oil.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue dissolved in ethyl acetate
  3. washwashed with aqueous LiCl (4 w/w), 0.1 M HCl and saturated NaHCO3

Sources & evidence

ORD record
ord-0c9d88b28b5440678ebc7878f3d04a87
Source dataset
uspto-grants-2013_04
Patent number
US08426420B2

Reaction notes

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