Triethylamine → (3S)-2-Oxo-3-benzoylamino-5-(3-phenylpropionyl)-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine-1-acetic acid methyl ester

HRID 1384720Notes

Reaction equation

HRID 1384720 reaction equation
[CH3:1][O:2][C:3](=[O:29])[CH2:4][N:5]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2C=CC[NH:9][CH2:8][C@H:7]([NH:19][C:20](=[O:27])[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:6]1=[O:28].C(N(CC)CC)C.[C:37]1([CH2:43][CH2:44][C:45](Cl)=[O:46])[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:29])[CH2:4][N:5]1[C:14]2[CH:13]=[CH:18][CH:17]=[CH:16][C:15]=2[N:9]([C:45](=[O:46])[CH2:44][CH2:43][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH2:8][C@H:7]([NH:19][C:20](=[O:27])[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:6]1=[O:28]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 64801Benzenepropanoyl chlorideHCID 70235204(3S)-2-oxo-3-(benzoylamino)-2,3,4,5-tetrahydro-1H-1,5-benzodiazecine-1-acetic acid methyl ester

Product 1

HCID 57159598(3S)-2-Oxo-3-benzoylamino-5-(3-phenylpropionyl)-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine-1-acetic acid methyl esterYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of (3S)-2-oxo-3-(benzoylamino)-2,3,4,5-tetrahydro-1H-1,5-benzodiazecine-1-acetic acid methyl ester 200 mg, 0.57 mmol) in CH2Cl2(10 ml) was treated with triethylamine (1-9 mg, 1.13 mmol) and 3-phenylpropionyl chloride (114 mg, 0.68 mmol). The reaction was stirred at RT for 30 min and diluted with CH2Cl2. The solution was washed wIth*. aq. 10% HCl, sat. aq. NaHCO3 and sat. aq. NaCl, dried over Na2SO4 and concentrated in vacuo to give 240 mg (87%) of 602a as a white foam.

Workup

  1. washThe solution was washed wIth*
  2. dry with materialaq. 10% HCl, sat. aq. NaHCO3 and sat. aq. NaCl, dried over Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-505d2bc5bd4c46ebbe9439b0afddee6e
Source dataset
uspto-grants-2001_07
Patent number
US06258948B1

Reaction notes

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