Diethyl Ether → (S)-2-(phenoxathiine-2-sulfonylamino)-4-phenyl-butyric acid

HRID 1953391Notes

Reaction equation

HRID 1953391 reaction equation
[CH:1]1[C:14]2[S:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[O:6][C:5]=2[CH:4]=[CH:3][C:2]=1[S:15](Cl)(=[O:17])=[O:16].[NH2:19][C@H:20]([C:29]([OH:31])=[O:30])[CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(N(CC)CC)C.C(OCC)C>O.O1CCCC1>[CH:1]1[C:14]2[S:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[O:6][C:5]=2[CH:4]=[CH:3][C:2]=1[S:15]([NH:19][C@@H:20]([CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:29]([OH:31])=[O:30])(=[O:17])=[O:16]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 2724505(S)-2-amino-4-phenylbutanoic acidHCID 15487618Phenoxathiine-2-sulfonyl chloride

Product 1

HCID 15487605(S)-2-(phenoxathiine-2-sulfonylamino)-4-phenyl-butyric acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

The phenoxathiine-2-sulfonyl chloride (0.75 g, 2.52 mmol) was mixed with (L)-homo-phenylalanine (0.448 g, 2.52 mmol) and triethylamine (1.2 mL, 7.56 mmol) in 50 mL of water and 50 mL of tetrahydrofuran. The resulting mixture was stirred for 2 hours and then concentrated in vacuo. The residue was partitioned between 1 M HCl and ethyl acetate. The organic phase was dried over magnesium sulfate, and concentrated to give an oily solid. Trituration with diethyl ether gave (S)-2-(phenoxathiine-2-sulfonylamino)-4-phenyl-butyric acid as an off-white powder; mp 149-154° C.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was partitioned between 1 M HCl and ethyl acetate
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. concentrationconcentrated
  5. customto give an oily solid

Sources & evidence

ORD record
ord-48a3d83dc5074836a50639a5b1759fc4
Source dataset
uspto-grants-2000_09
Patent number
US06117869

Reaction notes

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