3(S)-(2-((2(S)-Benzoylamino-3-methylbutyryl)benzylamino)acetylamino)-4-(4-(2,6-dichlorophenyl)-oxazol-2-yl)-4-hydroxybutyric Acid tert-Butyl Ester → 3(S)-(2-((2(S)-Benzoylamino-3-methylbutyryl)benzylamino)acetylamino)-4-(4-(2,6-dichlorophenyl)-oxazol-2-yl)-4-oxobutyric Acid tert-Butyl Ester

HRID 1456652Notes

Reaction equation

HRID 1456652 reaction equation
[C:1]([O:5][C:6](=[O:51])[CH2:7][C@H:8]([NH:24][C:25](=[O:50])[CH2:26][N:27]([C:35](=[O:49])[C@@H:36]([NH:40][C:41](=[O:48])[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[CH:37]([CH3:39])[CH3:38])[CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH:9]([C:11]1[O:12][CH:13]=[C:14]([C:16]2[C:21]([Cl:22])=[CH:20][CH:19]=[CH:18][C:17]=2[Cl:23])[N:15]=1)[OH:10])([CH3:4])([CH3:3])[CH3:2]>C(Cl)Cl>[C:1]([O:5][C:6](=[O:51])[CH2:7][C@H:8]([NH:24][C:25](=[O:50])[CH2:26][N:27]([C:35](=[O:49])[C@@H:36]([NH:40][C:41](=[O:48])[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[CH:37]([CH3:39])[CH3:38])[CH2:28][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[C:9]([C:11]1[O:12][CH:13]=[C:14]([C:16]2[C:17]([Cl:23])=[CH:18][CH:19]=[CH:20][C:21]=2[Cl:22])[N:15]=1)=[O:10])([CH3:3])([CH3:4])[CH3:2]

Participants

3

Reactant 1

HCID 544408483(S)-(2-((2(S)-Benzoylamino-3-methylbutyryl)benzylamino)acetylamino)-4-(4-(2,6-dichlorophenyl)-oxazol-2-yl)-4-hydroxybutyric Acid tert-Butyl Ester

Product 1

HCID 541815803(S)-(2-((2(S)-Benzoylamino-3-methylbutyryl)benzylamino)acetylamino)-4-(4-(2,6-dichlorophenyl)-oxazol-2-yl)-4-oxobutyric Acid tert-Butyl EsterYield 50.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of Dessmarten (259 mg, 0.61 mmol) in CH2Cl2 (4.0 mL) was added dropwise a solution of compound 708 (150 mg, 0.20 mmol) in CH2Cl2 (2.0 mL). After stirring at rt for 1 hr. the reaction was concentrated in vacuo. The residue was dissolved into EtOAc and washed with 1:1 sat. aq. Na2S2O3 :sat. aq. NaHCO3, sat. aq. NaHCO3, brine, dried over MgSO4, filtered and concentrated in vacuo. Chromatography on silica gel (elution with 2-5% MeOH:CH2 Cl2) provided 74 mg of compound 709. ##STR88##

Workup

  1. concentrationthe reaction was concentrated in vacuo
  2. dissolutionThe residue was dissolved into EtOAc
  3. washwashed with 1:1 sat. aq. Na2S2O3
  4. dry with materialaq. NaHCO3, sat. aq. NaHCO3, brine, dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-97811ef0d3a544babd88a3f51a6e020d
Source dataset
uspto-grants-1998_12
Patent number
US05843904

Reaction notes

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