Cesium carbonate → HCID 68750611, compound

HRID 334853

Reaction equation

HRID 334853 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[C:7]([O:11][C:12]([NH:14][C@@H:15]([C:18]([O:20][CH3:21])=[O:19])[CH2:16]I)=[O:13])([CH3:10])([CH3:9])[CH3:8].[Cl:22][C:23]1[CH:24]=[C:25]([CH2:29][C:30](=[O:32])[CH3:31])[CH:26]=[CH:27][CH:28]=1>CN(C=O)C>[C:7]([O:11][C:12]([NH:14][CH:15]([CH2:16][CH:29]([C:25]1[CH:26]=[CH:27][CH:28]=[C:23]([Cl:22])[CH:24]=1)[C:30](=[O:32])[CH3:31])[C:18]([O:20][CH3:21])=[O:19])=[O:13])([CH3:10])([CH3:9])[CH3:8]

Participants

5

Reactant 3

HCID 10796Cesium carbonate2×HCID 27340971-(3-Chlorophenyl)propan-2-oneHCID 11416215(S)-Methyl 2-Boc-amino-3-iodopropionate

Product 1

HCID 68750611HCID 68750611, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of cesium carbonate (9.80 g, 30.1 mmol) and methyl N-(tert-butoxycarbonyl)-3-iodo-D-alaninate (9.90 g, 30.1 mmol) in DMF (75 mL) was stirred at 23° C. for 45 min before 1-(3-chlorophenyl)propan-2-one (6.09 g, 36.1 mmol) and additional cesium carbonate (9.80 g, 30.1 mmol) were added. The resulting mixture was stirred for 2.5 h. The majority of the DMF was then removed under reduced pressure at a bath temperature of <40° C. The concentrated mixture was partitioned between water (500 mL) and ethyl acetate (2×200 mL). The combined organic layers were washed with brine, dried over sodium sulfate and concentrated to give the title compound as a 1:1 racemic mixture of diastereomers, which was used without further purification. MS: m/z=314.1 (M−t-Bu+1).

Workup

  1. additionwere added
  2. customThe majority of the DMF was then removed under reduced pressure at a bath temperature of <40° C
  3. customThe concentrated mixture was partitioned between water (500 mL) and ethyl acetate (2×200 mL)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1a8105477be645fc9d9f54dd540a2c0e
Source dataset
uspto-grants-2014_11
Patent number
US08883807B2

Linked notes

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