Triethylamine → N-[(2-Fluorophenyl)sulfonyl]-D-phenylalanine

HRID 1479920Notes

Reaction equation

HRID 1479920 reaction equation
C([O:5][C:6](=[O:16])[C@@H:7]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[NH2:8])(C)(C)C.C(N(CC)CC)C.[F:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[S:31](Cl)(=[O:33])=[O:32]>ClCCl>[F:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[S:31]([NH:8][C@H:7]([CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:6]([OH:5])=[O:16])(=[O:33])=[O:32]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1377612-Fluorobenzenesulphonyl chlorideHCID 11085361D-Phenylalanine 1,1-dimethylethyl ester

Product 1

HCID 2062364N-[(2-Fluorophenyl)sulfonyl]-D-phenylalanine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of A1 (110.65 mg, 0.5 mmol) in dry dichloromethane (3 mL) at 0° C. was added triethylamine (0.086 mL, 0.55 mmol) and 2-fluorobenzenesulfonyl chloride (66.88 μL, 0.50 mmol). The reaction mixture was stirred at room temperature overnight and concentrated under reduced pressure. Then dissolved the oil mixture in 2 mL CH2Cl2 and 2 mL TFA was add under argon. The reaction mixture was stirred at room temperature for 12 h (TLC monitor). The solvent was removed under reduce pressure and the crude compound was purified by flash chromatography on silica gel, using ethyl acetate/hexane (2:5) as the eluent, gave 14a; (105.42 mg, 65.2%). [α]D25: −11.7 (c=0.24, CHCl3); 1H-NMR (300 MHz, CDCl3): δ 7.82 (dd, J=1.8, 7.8 Hz, 1H), 7.60-7.52 (m, 1H), 7.27-7.21 (m, 4H), 7.16-7.09 (m, 3H), 5.27 (d, J=9 Hz, 1H), 4.41 (m, 1H), 3.20-3.06 (m, 2H); 13C NMR (300 MHz, acetone-d6): δ 171.41, 160.51, 157.15, 136.54, 134.91, 134.80, 129.48, 129.31, 128.18, 126.68, 124.15, 117.04, 116.76, 57.31, 38.36; HRMS (ESI): calcd for: C15H14FNO4S [M+H]+=324.0690, obsd [M+H]+=324.0700.

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThen dissolved the oil mixture in 2 mL CH2Cl2
  3. addition2 mL TFA was add under argon
  4. stirringThe reaction mixture was stirred at room temperature for 12 h (TLC monitor)
  5. customThe solvent was removed
  6. customthe crude compound was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-fc351ef51bc944a5a179c4e26c14d2cb
Source dataset
uspto-grants-2016_08
Patent number
US09409880B2

Reaction notes

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