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

HRID 1643384Notes

Reaction equation

HRID 1643384 reaction equation
[CH2:1]([O:8][C:9](=[O:38])[CH2:10][N:11]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[N:15]([C:22](=[O:27])[CH2:23]C(C)=O)[CH2:14][C@H:13]([NH:28]C(=O)C2C=CC=CC=2)[C:12]1=[O:37])C1C=CC=CC=1.[CH2:39](OC(=O)CN1C2C=CC=CC=2NC[C@H](NC(OC(C)(C)C)=O)C1=O)[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1.[C:70]([OH:76])(=O)[CH2:71][C:72]([CH3:74])=O.Cl.CN(C)[CH2:80][CH2:81][CH2:82]N=C=NCC>C(Cl)Cl>[CH3:1][O:8][C:9](=[O:38])[CH2:10][N:11]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[N:15]([C:22](=[O:27])[CH2:23][CH2:39][C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[CH2:14][C@H:13]([NH:28][C:70](=[O:76])[C:71]2[CH:72]=[CH:74][CH:82]=[CH:81][CH:80]=2)[C:12]1=[O:37]

Participants

6

Reactant 4

HCID 96Acetoacetic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57080557(3S)-2-oxo-3-benzoylamino-5-acetoacetyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine-1-acetic acid benzyl esterHCID 57313411HCID 57313411, compound

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 ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

Method B. (3S)-2-oxo-3-benzoylamino-5-acetoacetyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine-1-acetic acid benzyl ester (602g). A 0° C. solution of (3S)-2-oxo-3-(benzoylamino)-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine-1-acetic acid benzyl ester (600b) (465 mg, 1.10 mmol) in CH2Cl2 (5 ml) was treated with acetoacetic acid in 1 ml of CH2Cl2 followed by slow addition of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (431 mg, 2.2 mmol) in 2 ml of CH2Cl2 under N2 atmosphere. After 15 min the reaction was poured onto EtOAc, washed with aq. 5% NaHSO4, dried over Na2SO4 and concentrated in vacuo.

Workup

  1. additionAfter 15 min the reaction was poured onto EtOAc
  2. washwashed with aq. 5% NaHSO4
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2b90de2cd0814da4b103e29798e5e1b5
Source dataset
uspto-grants-2012_02
Patent number
US08119631B2

Reaction notes

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