Triethylamine → HCID 68604076, compound

HRID 2267609Notes

Reaction equation

HRID 2267609 reaction equation
[CH2:1]([O:8][C:9]([NH:11]/[C:12](=[CH:17]\[C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([Cl:25])[CH:19]=1)/[C:13]([O:15][CH3:16])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[SH:33].C(N(CC)CC)C>CO>[NH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[S:33][CH:17]([C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([Cl:25])[CH:19]=1)[C@@H:12]([C:13]([O:15][CH3:16])=[O:14])[NH:11][C:9]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:10]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 87132-AminothiophenolHCID 86604631HCID 86604631, compound

Product 1

HCID 68604076HCID 68604076, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a deoxygenated solution of methyl (2Z)-2-{[(benzyloxy)carbonyl]amino}-3-(3,4-dichlorophenyl)acrylate (10a) (2.17 g, 5.7 mmol) in anhydrous methanol (40 ml) (warmed to dissolve) under nitrogen was added the 2-aminothiophenol (3.1 ml, 28.5 mmol) followed by addition of triethylamine (400 ul, 2.85 mmol). The mixture stirred 3 days at ambient temperature, concentrated to ca. 10 mL, partitioned between cold 1N hydrochloric acid (75 mL) and ethyl acetate (100 mL). The organic phase was separated and consecutively washed with 1N hydrochloric acid (4×), dilute aqueous sodium bicarbonate and brine, dried, filtered and evaporated to give the title compound (10b) as an 4:1 mixture (erythro:threo) (2.8 g, 96%). A 100 mg sample was converted to the HCl salt to provide an analytically pure title compound (32 mg) as a (4:1) mixture. MS APCI, m/z=505 (M+1), 507 (M+3). LC/MS: 2.94 min.

Workup

  1. concentrationconcentrated to ca. 10 mL
  2. custompartitioned between cold 1N hydrochloric acid (75 mL) and ethyl acetate (100 mL)
  3. customThe organic phase was separated
  4. washconsecutively washed with 1N hydrochloric acid (4×), dilute aqueous sodium bicarbonate and brine
  5. customdried
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-419fec0aa9094634b11650e37989a508
Source dataset
uspto-grants-2010_12
Patent number
US07858776B2

Reaction notes

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