Hydrochloric Acid → HCID 44349654, compound

HRID 5423Notes

Reaction equation

HRID 5423 reaction equation
C([S:4][CH2:5][CH:6]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][S:11][CH2:10][C@@H:9]([C:20]([O:22]CC2C=CC=CC=2)=[O:21])[NH:8][C:7]1=[O:30])(=O)C.O.[OH-].[Li+].Cl>>[SH:4][CH2:5][CH:6]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][S:11][CH2:10][C@@H:9]([C:20]([OH:22])=[O:21])[NH:8][C:7]1=[O:30]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 44349442Benzyl (3R)-6-(acetylthiomethyl)-5-oxo-1-thia-4-azacyclotetradecane-3-carboxylate

Product 1

HCID 44349654HCID 44349654, compound

Procedure

Benzyl (3R)-6-(acetylthiomethyl)-5-oxo-1-thia-4-azacyclotetradecane-3-carboxylate (Isomer A), (0.11 g, 0.25 mmol) is dissolved in nitrogen degassed tetrahydrofuran (5 ml) and water (1 ml). Lithium hydroxide monohydrate (0.032 g, 0.75 mmol) is added and the mixture is stirred for 3 hours at room temperature. The mixture is poured into 1N hydrochloric acid and extracted with ethyl acetate (2×50 ml). The combined organic layers are washed with brine (1×50 ml), dried (MgSO4) and the solvent is evaporated. The product is triturated from diethyl ether/hexane (1:1) to give (3R)-6-mercaptomethyl-5-oxo-1-thia-4-azacyclotetradecane-3-carboxylic acid (Isomer A), m.p. 165°-168° C.

Workup

  1. customdegassed tetrahydrofuran (5 ml) and water (1 ml)
  2. extractionextracted with ethyl acetate (2×50 ml)
  3. washThe combined organic layers are washed with brine (1×50 ml)
  4. dry with materialdried (MgSO4)
  5. customthe solvent is evaporated
  6. customThe product is triturated from diethyl ether/hexane (1:1)

Sources & evidence

ORD record
ord-87d288d6baf14569856e62b2735e05e2
Source dataset
uspto-grants-1993_09
Patent number
US05244889

Reaction notes

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