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

HRID 5422ノート

反応式

HRID 5422 の反応式
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]

参加物

4

反応物 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

生成物 1

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

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-dd987d53ad42490d9a6acf8aa6747c75
出典データセット
uspto-grants-1993_09
特許番号
US05244889

反応ノート

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