Water → (Rac)-4-(3-hydroxy-1-methoxymethyl-propyl)-5-oxo-[1,4]diazepane-1-carboxylic acid benzyl ester

HRID 655508Notes

Reaction equation

HRID 655508 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH2:19]([O:26][C:27]([N:29]1[CH2:35][CH2:34][C:33](=[O:36])[N:32]([CH:37]([CH2:48][O:49][CH3:50])[CH2:38][CH2:39][O:40][Si](C(C)(C)C)(C)C)[CH2:31][CH2:30]1)=[O:28])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.O>O1CCCC1>[CH2:19]([O:26][C:27]([N:29]1[CH2:35][CH2:34][C:33](=[O:36])[N:32]([CH:37]([CH2:48][O:49][CH3:50])[CH2:38][CH2:39][OH:40])[CH2:31][CH2:30]1)=[O:28])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 67080682(Rac)-4-[3-(tert-butyl-dimethyl-silanyloxy)-1-methoxymethyl-propyl]-5-oxo-[1,4]diazepane-1-carboxylic acid benzyl ester

Product 1

HCID 67080771(Rac)-4-(3-hydroxy-1-methoxymethyl-propyl)-5-oxo-[1,4]diazepane-1-carboxylic acid benzyl esterYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3.22 ml (3.22 mmol, 1 M in tetrahydrofuran) tetrabutylammonium fluoride were added to a cooled solution (0° C.) of 1.36 g (2.93 mmol) (rac)-4-[3-(tert-butyl-dimethyl-silanyloxy)-1-methoxymethyl-propyl]-5-oxo-[1,4]diazepane-1-carboxylic acid benzyl ester in 29 ml tetrahydrofuran. After 50 min water was added and extracted with ethyl acetate (3×). The organic phases were washed with water (2×), dried over Na2SO4 and evaporated. Flash chromatography on silica gel with a gradient 2% to 4% methanol in dichloromethane yielded 0.79 g (77%) of the title compound as a colorless oil, MS: 263 (M).

Workup

  1. extractionextracted with ethyl acetate (3×)
  2. washThe organic phases were washed with water (2×)
  3. dry with materialdried over Na2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-8396006342164e29acce9d348244cd41
Source dataset
uspto-grants-2011_12
Patent number
US08071586B2

Reaction notes

Loading…