Hydrochloric Acid → HCID 44349654, 화합물

HRID 5423노트

반응식

HRID 5423 반응식
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]

참가 물질

4

반응물 3

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

생성물 1

HCID 44349654HCID 44349654, 화합물

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-87d288d6baf14569856e62b2735e05e2
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05244889

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