Triethylamine → 2-(4-Methoxy-2,3,6-trimethyl-benzenesulfonylamino)-3-phenyl-propionic acid methyl ester

HRID 2179925Notes

Reaction equation

HRID 2179925 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C@H:4]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[NH2:5].C(N(CC)CC)C.[CH3:21][O:22][C:23]1[CH:28]=[C:27]([CH3:29])[C:26]([S:30](Cl)(=[O:32])=[O:31])=[C:25]([CH3:34])[C:24]=1[CH3:35]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:1][O:2][C:3](=[O:13])[CH:4]([NH:5][S:30]([C:26]1[C:27]([CH3:29])=[CH:28][C:23]([O:22][CH3:21])=[C:24]([CH3:35])[C:25]=1[CH3:34])(=[O:32])=[O:31])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 5627874-Methoxy-2,3,6-trimethylbenzenesulfonyl chlorideHCID 736234L-Phenylalanine, methyl ester

Product 1

HCID 50165302-(4-Methoxy-2,3,6-trimethyl-benzenesulfonylamino)-3-phenyl-propionic acid methyl ester

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of L-phenylalanine methyl ester (300 mg, 1.68 mmol) in anhydrous CH2Cl2 (10 mL) was cooled to 0° C. in an ice bath, then triethylamine (0.35 mL), 4-methoxy-2,3,6-trimethyl-benzenesulfonyl chloride (438 mg, 1.76 mmol) and catalytic amount of DMAP (25 mg) were added under a N2 atmosphere. The reaction mixture was stirred at room temperature for 12 h. After that period of time, the mixture was partitioned between water and CH2Cl2, the organic layer was separated, dried (Na2SO4) and concentrated. The residue was purified by silica gel column chromatography using ethyl acetate and hexane (1:2) as eluent to obtain 2-(4-Methoxy-2,3,6-trimethyl-benzenesulfonylamino)-3-phenyl-propionic acid methyl ester as a white solid, 500 mg (77%). 1H NMR (CDCl3, 400 MHz): δ7.26-7.18 (m, 3H), 7.02-6.99 (m, 2H), 6.53 (s, 1H), 5.12 (d, 1H), 4.09-4.04 (m, 1H), 3.84 (s, 3H), 3.55 (s, 3H), 3.05 (dd, 1H), 3.03 (dd, 1H), 2.64, 2.38, 2.08 (3s, 9H).

Workup

  1. waitAfter that period of time
  2. customthe mixture was partitioned between water and CH2Cl2
  3. customthe organic layer was separated
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-db201fb0ba5c48e3831ed0446dc452e2
Source dataset
uspto-grants-2005_05
Patent number
US06887877B2

Reaction notes

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