HCID 11384414, compound → HCID 86750209, compound

HRID 234216Notes

Reaction equation

HRID 234216 reaction equation
C[O:2][C:3]([C@H:5]1[NH:17][C:16](=[S:18])[CH2:15][CH2:14][CH2:13][O:12][C:11](=[O:19])[C:10]2[C:20]([CH3:27])=[C:21]([O:25][CH3:26])[CH:22]=[C:23]([OH:24])[C:9]=2[CH2:8][S:7][CH2:6]1)=O>CO.C(N)C=C>[CH2:16]([NH:17][C:3]([C@H:5]1[NH:17][C:16](=[S:18])[CH2:15][CH2:14][CH2:13][O:12][C:11](=[O:19])[C:10]2[C:20]([CH3:27])=[C:21]([O:25][CH3:26])[CH:22]=[C:23]([OH:24])[C:9]=2[CH2:8][S:7][CH2:6]1)=[O:2])[CH:15]=[CH2:14]

Participants

4

Reactant 1

HCID 11384414HCID 11384414, compound

Product 1

HCID 86750209HCID 86750209, compoundYield 147.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 7853AllylamineSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 124 mg of (R)-15-hydroxy-13-methoxy-12-methyl-11-oxo-6-thioxo-3,4,5,6,7,8,9,11-octahydro-1H-10,2,5-benzoxathiaazacyclo-tridecine-4-carboxylic acid methyl ester in a mixture of 1.5 ml of methanol and 1.5 ml of allylamine was heated to 50° C. for 2.5 h. The solution was evaporated in vacuo. The residue was chromatographed on silica gel using ethyl acetate/hexane (2:1, v/v) as eluent, and the purified product was crystallized from ethyl acetate/hexane to afford 97 mg of (R)-15-hydroxy-13-methoxy-12-methyl-11-oxo-6-thioxo-3,4,5,6,7,8,9,11-octahydro-1H-10,2,5-benzoxathiaazacyclotridecine-4-carboxylic acid allylamide as a white solid.

Workup

  1. customThe solution was evaporated in vacuo
  2. customThe residue was chromatographed on silica gel
  3. customv/v) as eluent, and the purified product was crystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-77daebbaded043198155fe92fd616934
Source dataset
uspto-grants-1997_01
Patent number
US05594135

Reaction notes

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