Methyl (4R)-1,3,4,5,6,7,8,9,10,12-decahydro-16-hydroxy-14-methoxy-13-methyl-12-oxo-6-thioxo-11,2,5-benzoxathiaazacyclotetradecine-4-carboxylate → HCID 54464536, compound

HRID 234217Notes

Reaction equation

C[O:2][C:3]([C@H:5]1[NH:18][C:17](=[S:19])[CH2:16][CH2:15][CH2:14][CH2:13][O:12][C:11](=[O:20])[C:10]2[C:21]([CH3:28])=[C:22]([O:26][CH3:27])[CH:23]=[C:24]([OH:25])[C:9]=2[CH2:8][S:7][CH2:6]1)=O>CO.C(N)CC>[CH2:17]([NH:18][C:3]([C@H:5]1[NH:18][C:17](=[S:19])[CH2:16][CH2:15][CH2:14][CH2:13][O:12][C:11](=[O:20])[C:10]2[C:21]([CH3:28])=[C:22]([O:26][CH3:27])[CH:23]=[C:24]([OH:25])[C:9]=2[CH2:8][S:7][CH2:6]1)=[O:2])[CH2:16][CH3:15]

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of 43 mg of the product of Example 23 in a mixture of 0.5 ml of methanol and 0.5 ml of propylamine was heated to 50° C. for 6 h. The solution was evaporated in vacuo, the residue was dissolved in ethyl acetate and the solution was washed with 1N hydrochloric acid and water. The organic layer was dried over sodium sulfate and evaporated in vacuo, the residue was chromatographed on silica gel using ethyl acetate/hexane (1:2, v/v) as eluent, and the purified product was crystallized from ethyl acetate/hexane to afford 22 mg of (R)-16-hydroxy-14-methoxy-13-methyl-12-oxo-6-thioxo-1,3,4,5,6,7,8,9,10,12-decahydro-11,2,5-benzoxathiaazacyclotetradecine-4-carboxylic acid propylamide as a white solid.

Workup

customThe solution was evaporated in vacuo
dissolutionthe residue was dissolved in ethyl acetate
washthe solution was washed with 1N hydrochloric acid and water
dry with materialThe organic layer was dried over sodium sulfate
customevaporated in vacuo
customthe residue was chromatographed on silica gel
customv/v) as eluent, and the purified product was crystallized from ethyl acetate/hexane

Sources & evidence

ORD record: ord-ace809e2b1ff4e3585639cda64c9772b
Source dataset: uspto-grants-1997_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05594135

Reaction notes

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