Hydrochloric Acid → HCID 178443479, compound

HRID 1440520Notes

Reaction equation

HRID 1440520 reaction equation
Br[C@H:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[C:3]([OH:5])=O.C[C:15]([CH3:18])([O-])[CH3:16].[K+].C([SH:26])CCCCC.Cl.[CH2:28]1[CH2:32]OC[CH2:29]1>>[CH2:29]([C@@H:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[C:3]([OH:5])=[S:26])[CH2:28][CH2:32][CH2:16][CH2:15][CH3:18]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 81061-HexanethiolHCID 23665647Potassium tert-butoxideHCID 54003828(R)-2-bromodecanoic acid

Product 1

HCID 178443479HCID 178443479, compoundYield 80%

Procedure

Using the procedure outlined in Example 33, (R)-2-bromodecanoic acid (0.374 g, 1.49 mmol) was treated with potassium tert-butoxide (0.480 g, 4.28 mmol) in THF (9 mL) at 0° C. Hexanethiol (0.30 mL, 2.02 mmol) was added dropwise and the reaction was stirred for 18 hours. The reaction was poured into 1N HCl (25 mL) and extracted with hexane (2×25 mL). The combined organic layers were washed with NaHCO3 solution (25 mL, 0.5M), followed by HCl (1N, 25 mL) and dried (MgSO4). Following solvent removal, (S)-hexylthiodecanoic acid (0.34 g, 1.18 mmol, 80%) was obtained. This material was judged to be 95% ee.

Workup

  1. extractionextracted with hexane (2×25 mL)
  2. washThe combined organic layers were washed with NaHCO3 solution (25 mL, 0.5M)
  3. dry with materialdried (MgSO4)
  4. customFollowing solvent removal

Sources & evidence

ORD record
ord-705d5a74eb9342378b2683aa9bba0303
Source dataset
uspto-grants-1996_03
Patent number
US05498786

Reaction notes

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