Dimethyl Sulfide → HCID 68555151, compound

HRID 714145Notes

Reaction equation

HRID 714145 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=1)[C:10](O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].CSC>C1COCC1>[C:1]([O:5][C:6](=[O:7])[NH:8][C@@H:9]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=1)[CH2:10][OH:11])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 1068Dimethyl SulfideHCID 2761816Boc-3-Nitro-L-Phenylalanine

Product 1

HCID 68555151HCID 68555151, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-2-(tert-butoxycarbonylamino)-3-(3-nitrophenyl)propanoic acid (562 mg, 1.8 mmol) in THF (9 ml) stirred at 0° C. under N2 atmosphere, 10 M solution of BH3.DMS (0.5 ml, 5.27 mmol) was slowly added, after addition was completed the final mixture was warmed to room temperature and stirred for further 6 h. Cooled down to 0° C., quenched with water, diluted with DCM and washed with 10% K2CO3 solution in water; dried over MgSO4, filtered and concentrated to afford 432mg (80% yield) of an oil which was submitted to the next step without further purification. MS: m/z=319.1 (MH+)

Workup

  1. additionafter addition
  2. temperatureCooled down to 0° C.
  3. customquenched with water
  4. additiondiluted with DCM
  5. washwashed with 10% K2CO3 solution in water
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-1a74f2590f5b4c3892564808f7b4931b
Source dataset
uspto-grants-2015_11
Patent number
US09187415B2

Reaction notes

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