Hydrochloric Acid → HCID 57110839, compound

HRID 2414591Notes

Reaction equation

HRID 2414591 reaction equation
[NH2:1][C@H:2]([C:6]([S:9][CH2:10][CH2:11][CH2:12][OH:13])([CH3:8])[CH3:7])[C:3]([OH:5])=[O:4].[CH2:14](N(CC)CC)[CH3:15].C(O[C:26]1[CH:31]=CC=[CH:28][C:27]=1[S:32](Cl)(=[O:34])=[O:33])#CCC.Cl.O1[CH2:42][CH2:41][O:40][CH2:39][CH2:38]1.O>>[CH2:39]([O:40][C:41]1[CH:42]=[CH:28][C:27]([S:32]([NH:1][C@H:2]([C:6]([S:9][CH2:10][CH2:11][CH2:12][OH:13])([CH3:8])[CH3:7])[C:3]([OH:5])=[O:4])(=[O:34])=[O:33])=[CH:26][CH:31]=1)[C:38]#[C:14][CH3:15]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 218864351,4-Dioxane--water (1/1)HCID 57144254HCID 57144254, compoundHCID 86587116HCID 86587116, compound

Product 1

HCID 57110839HCID 57110839, compoundYield 83%

Procedure

The (2S)-2-amino-3-[(3-hydroxypropyl)sulfanyl]-3-methylbutanoic acid was dissolved in dioxane:water (1:1) (40 mL). Triethylamine (5.1 mL, 50.4 mmol) was added to the solution followed by 2-butynyloxybenzenesulfonyl chloride (4.1 g, 16.8 mmol). The resulting mixture was stirred for 15 h at room temperature. The mixture was acidified to pH˜2 with 1N hydrochloric acid and partitioned between ethyl acetate and water. The organic layer was dried over anhydrous sodium sulfate. Removal of the solvent gave 5.78 g (83%) of (2S)-2-({[4-(2-butynyloxy)phenyl]sulfonyl}amino)-3-[(3-hydroxypropyl)sulfanyl]-3-methylbutanoic acid as a solid; 1H NMR (300 MHz, acetone-d6) δ 1.34 (s, 3H), 1.39 (s, 3H), 1.66 (m, 2H), 2.06 (m, 3H), 2.54-2.68 (m, 2H), 3.89 (m, 1H), 4.82 (m, 2H), 6.56 (d, 1H, J=9.0 Hz), 7.12(d, 2H, J=8.7 Hz), 7.81(d, 2H, J=8.7 Hz). HRMS (C18H25NOS2)(M+H); calcd. 416.1196, found 416.1199.

Workup

  1. custompartitioned between ethyl acetate and water
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. customRemoval of the solvent

Sources & evidence

ORD record
ord-4ecbffd4462f4f9ca9b79586056b2898
Source dataset
uspto-grants-2004_11
Patent number
US06812227B2

Reaction notes

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