2,2-Dimethoxypropane → tert-butyl (4S,5S)-4-benzyl-5-[2-{[(benzyloxy)carbonyl]amino}-3-(4-bromophenyl)propyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

HRID 1174332Notes

Reaction equation

HRID 1174332 reaction equation
[Br:1][C:2]1[CH:39]=[CH:38][C:5]([CH2:6][CH:7]([NH:27][C:28](=[O:37])[O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH2:8][C@H:9]([OH:26])[C@@H:10]([NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.CO[C:49](OC)([CH3:51])[CH3:50]>O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH2:11]([C@H:10]1[C@H:9]([CH2:8][CH:7]([NH:27][C:28]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[O:37])[CH2:6][C:5]2[CH:38]=[CH:39][C:2]([Br:1])=[CH:3][CH:4]=2)[O:26][C:49]([CH3:51])([CH3:50])[N:18]1[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 64952,2-DimethoxypropaneHCID 8471TriethylamineHCID 86726232benzyl(3S,4S)-1-(4-bromobenzyl)-4-[(tert-butoxycarbonyl)amino]-3-hydroxy-5-phenylpentylcarbamate

Product 1

HCID 67406532tert-butyl (4S,5S)-4-benzyl-5-[2-{[(benzyloxy)carbonyl]amino}-3-(4-bromophenyl)propyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylateYield 54%

Reagents, catalysts & solvents 1

HCID 521998p-Toluenesulfonic acid monohydrateCatalyst

Conditions

Temperature
25 °C

Procedure

A solution containing the product from Example 128A (3.37 mmol) in 2,2-dimethoxypropane (35 mL) was treated with p-toluenesulfonic acid monohydrate (0.032 g, 0.17 mmol), stirred at 25° C. for 1 hour, treated with triethylamine (0.14 mL, 1.0 mmol), and the reaction was partitioned between ethyl acetate and water. The organic phase was washed with brine, dried over MgSO4, filtered and concentrated to give the product (1.16 g, 54% yield), which was used without further purification.

Workup

  1. customthe reaction was partitioned between ethyl acetate and water
  2. washThe organic phase was washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-cc6aac34cc2449429195b8f3eec3a41f
Source dataset
uspto-grants-2010_11
Patent number
US07834043B2

Reaction notes

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