2-Aminothiophenol → HCID 68029364, compound

HRID 714144Notes

Reaction equation

HRID 714144 reaction equation
[C:1]([O:5][C:6](=[O:30])[NH:7][C@@H:8]([CH2:28]Cl)[CH2:9][O:10][Si:11]([C:24]([CH3:27])([CH3:26])[CH3:25])([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([CH3:4])([CH3:3])[CH3:2].[NH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[SH:38].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.C(Cl)Cl>[C:1]([O:5][C:6](=[O:30])[NH:7][C@H:8]([CH2:9][O:10][Si:11]([C:24]([CH3:27])([CH3:26])[CH3:25])([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:28][S:38][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=1[NH2:31])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 87132-AminothiophenolHCID 10796Cesium carbonateHCID 68029366HCID 68029366, compound

Product 1

HCID 68029364HCID 68029364, compoundYield 103.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl[(2R)-1-{[tert-butyl(diphenyl)silyl]oxy}-3-chloropropan-2-yl]carbamate (58, 390 mg, 0.87 mmol) in dry DMF (2.5 ml) was treated with neat 2-aminobenzenethiol (351 mg, 2.8 mmol) followed by cesium carbonate (560 mg, 1.72 mmol). The mixture was stirred at room temperature for 3 h, diluted with DCM and washed with 1M NaOH followed by saturated NaHCO3, dried over MgSO4, filtered and concentrated to afford the title compound (482 mg) as an oil, which was submitted without further purification to the next synthetic step. MS: m/z=537.2 (MH+).

Workup

  1. washwashed with 1M NaOH
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-42e5aa8ccf4b4a82b2d4d5a2a124e29c
Source dataset
uspto-grants-2015_11
Patent number
US09187415B2

Reaction notes

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