Water → HCID 86699123, compound

HRID 1424210Notes

Reaction equation

HRID 1424210 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])[CH2:10][CH2:11][CH2:12][OH:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].CO[C:26](OC)([CH3:28])[CH3:27].CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1.O>C1COCC1>[CH3:27][C:26]1([CH3:28])[N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[C@@H:9]([C:14]([O:16][CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)=[O:15])[CH2:10][CH2:11][CH2:12][O:13]1

Participants

6

Reactant 4

HCID 962WaterHCID 64952,2-DimethoxypropaneHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 53858440N-[(1,1-Dimethylethoxy)carbonyl]-5-hydroxy-D-norvaline phenylmethyl ester

Product 1

HCID 86699123HCID 86699123, compoundYield 74.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To the solution of benzyl N-(tert-butoxycarbonyl)-5-hydroxy-D-norvalinate (Preparation 50, 3 g, 9.28 mmol) in THF (20 mL) was added 2,2-dimethoxypropane (12.07 mL, 92.8 mmol) and PPTS (catalytic amount), and the reaction was stirred for 5 hours at 60° C. The reaction mixture was poured into cold water and extracted with EtOAc. The organic layer was dried over Na2SO4 and concentrated under reduced pressure to afford the title compound (2.5 g, 74%).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-30da09b249a5497b938d90ee3b006f1c
Source dataset
uspto-grants-2015_01
Patent number
US08927587B2

Reaction notes

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