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

HRID 21995Notes

Reaction equation

HRID 21995 reaction equation
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]

Participants

4

Reactant 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

Product 1

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

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-49a71dae419145bb85402cdaff07ddf2
Source dataset
uspto-grants-1995_06
Patent number
US05426103

Reaction notes

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