Hydrochloric Acid → trans N-[[(3R)-6-mercaptomethyl-5-oxo-1-thia-4-azacyclotridecan-3-yl]-carbonyl]-4-hydroxy-L-proline

HRID 5422노트

반응식

HRID 5422 반응식
C([O:8][C:9](=[O:40])[C@@H:10]1[CH2:14][C@@H:13]([OH:15])[CH2:12][N:11]1[C:16]([C@H:18]1[NH:30][C:29](=[O:31])[CH:28]([CH2:32][S:33]C(=O)C(C)(C)C)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][S:20][CH2:19]1)=[O:17])C1C=CC=CC=1.O.[OH-].[Li+].Cl>>[SH:33][CH2:32][CH:28]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][S:20][CH2:19][C@@H:18]([C:16]([N:11]2[CH2:12][C@H:13]([OH:15])[CH2:14][C@H:10]2[C:9]([OH:40])=[O:8])=[O:17])[NH:30][C:29]1=[O:31]

참가 물질

4

반응물 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 54096127Trans-N-[(3R)-6-(pivaloylthiomethyl)-5-oxo-1-thia-4-azacyclotridecan-3-yl-carbonyl]-4-hydroxy-L-proline benzyl ester

생성물 1

HCID 53825878trans N-[[(3R)-6-mercaptomethyl-5-oxo-1-thia-4-azacyclotridecan-3-yl]-carbonyl]-4-hydroxy-L-proline

실험 절차

Trans-N-[(3R)-6-(pivaloylthiomethyl)-5-oxo-1-thia-4-azacyclotridecan-3-yl-carbonyl]-4-hydroxy-L-proline benzyl ester (0.30 g, 0.05 mmol) is dissolved in nitrogen degassed tetrahydrofuran (1 ml) and water (0.5 ml). Lithium hydroxide monohydrate (0.006 g, 0.15 mmol) is added and the mixture is stirred at room temperature for 2.5 hours. The mixture is poured into 1N hydrochloric acid and extracted with ethyl acetate (2×10 ml). The combined organic layers are dried (MgSO4) and the solvent is evaporated. The product is triturated from diethyl ether to give trans N-[[(3R)-6-mercaptomethyl-5-oxo-1-thia-4-azacyclotridecan-3-yl]-carbonyl]-4-hydroxy-L-proline, m.p. 124°-130° C.

후처리

  1. customdegassed tetrahydrofuran (1 ml) and water (0.5 ml)
  2. extractionextracted with ethyl acetate (2×10 ml)
  3. dry with materialThe combined organic layers are dried (MgSO4)
  4. customthe solvent is evaporated
  5. customThe product is triturated from diethyl ether

출처 및 근거

ORD 기록
ord-dd987d53ad42490d9a6acf8aa6747c75
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05244889

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