Benzoyl chloride → ((2(S)-Benzoylamino-3-methylbutyryl)benzylamino)acetic Acid Ethyl Ester

HRID 1456647Notes

Reaction equation

HRID 1456647 reaction equation
[CH2:1]([O:3][C:4](=[O:28])[CH2:5][N:6]([C:14](=[O:27])[C@@H:15]([NH:19][C:20]([O:22]C(C)(C)C)=O)[CH:16]([CH3:18])[CH3:17])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH3:2].CCN(C(C)C)C(C)C.C(Cl)(=O)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>CCOC(C)=O.Cl>[CH2:1]([O:3][C:4](=[O:28])[CH2:5][N:6]([C:14](=[O:27])[C@@H:15]([NH:19][C:20](=[O:22])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[CH:16]([CH3:17])[CH3:18])[CH2:7][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[CH3:2]

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 81531DiisopropylethylamineHCID 23402347Ethyl N-benzyl-N-((tert-butoxycarbonyl)-L-valyl)glycinate

Product 1

HCID 53936603((2(S)-Benzoylamino-3-methylbutyryl)benzylamino)acetic Acid Ethyl EsterYield 98.9%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of compound 702 (3.45 g, 8.8 mmol) in EtOAc at 0° C. was bubbled in gaseous HCl until saturated. The reaction was warmed to rt and stirred for 3 hr. Nitrogen was bubbled through the reaction to remove excess HCl, followed by concentration in vacuo. The residue suspended in CH2Cl2 (50 mL), treated with DIEA (3.4 mL, 19.5 mmol) followed by benzoyl chloride (1.2 mL, 10.3 mmol) and the reaction allowed to stir overnight. The reaction was concentrated in vacuo and the residue taken up into EtOAc and H2O. The layers were separated and the organic phase washed with sat. aq. NaHCO3, sat. aq. KHSO4, brine, dried over MgSO4, filtered and concentrated in vacuo to provide 3.45 g of compound 703. ##STR82##

Workup

  1. customNitrogen was bubbled through the reaction
  2. customto remove excess HCl
  3. concentrationfollowed by concentration in vacuo
  4. stirringto stir overnight
  5. concentrationThe reaction was concentrated in vacuo
  6. customThe layers were separated
  7. washthe organic phase washed with sat. aq. NaHCO3, sat. aq. KHSO4, brine
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a21eb8c73d2b4bda84cd88740187525e
Source dataset
uspto-grants-1998_12
Patent number
US05843904

Reaction notes

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