Methyl chloroformate → (3S)-2-Oxo-3-benzoylamino-5-methoxycarbonyl-2,3,4,5-tetrahydro-1H-1,5-benzo diazepine-1-acetic acid benzyl ester

HRID 2230466Notes

Reaction equation

HRID 2230466 reaction equation
[CH2:1]([O:8][C:9](=[O:31])[CH2:10][N:11]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[NH:15][CH2:14][C@H:13]([NH:22][C:23]([O:25]C(C)(C)C)=O)[C:12]1=[O:30])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:33]([O:35][CH3:36])=[O:34]>C1COCC1.C([O-])(O)=O.[Na+]>[CH2:1]([O:8][C:9](=[O:31])[CH2:10][N:11]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[N:15]([C:33]([O:35][CH3:36])=[O:34])[CH2:14][C@H:13]([NH:22][C:23](=[O:25])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:12]1=[O:30])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 6586Methyl chloroformateHCID 57313411HCID 57313411, compound

Product 1

HCID 66756270(3S)-2-Oxo-3-benzoylamino-5-methoxycarbonyl-2,3,4,5-tetrahydro-1H-1,5-benzo diazepine-1-acetic acid benzyl esterYield 201.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

A vigorously-stirred, 0° C. solution of (3S)-2-oxo-3-(benzoylamino)-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine-1-acetic acid benzyl ester (600b) (461 mg, 1.07 mmol) in THF (5 ml) and sat. aq. NaHCO3 (2.5 ml) was treated with a THF solution (0.35 ml) of methyl chloroformate (151 mg, 1.6 mmol) and the reaction was stirred for 45 min at RT. The reaction was poured onto CH2Cl2 and washed with H2O, dried over Na2SO4 and concentrated in vacuo. Chromatography (flash, SiO2, 0% to 10% MeOH/CH2Cl2) gave 525 mg of 602j as a white solid.

Workup

  1. additionThe reaction was poured onto CH2Cl2
  2. washwashed with H2O
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-df152e92662c4258ad37019f1a2f6d37
Source dataset
uspto-grants-2002_07
Patent number
US06423840B1

Reaction notes

Loading…