3-Amino-1-propanol → HCID 53693826, compound

HRID 234219Notes

Reaction equation

HRID 234219 reaction equation
CO[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:4].[NH2:29][CH2:30][CH2:31][CH2:32][OH:33]>CO.C(OCC)(=O)C>[OH:33][CH2:32][CH2:31][CH2:30][NH:29][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:4]

Participants

5

Reactant 2

HCID 90863-Amino-1-propanolHCID 9823853Methyl (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

Product 1

HCID 53693826HCID 53693826, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

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 3-amino-propanol was heated to 50° C. 20 min. The mixture was diluted with ethyl acetate and washed with 1N hydrochloric acid and water. The organic layer was dried over sodium sulfate and evaporated in vacuo and the solid residue was recrystallized from ethyl acetate/hexane to afford 12 mg (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 3-hydroxy-propylamide as a white solid.

Workup

  1. custom20 min
  2. washwashed with 1N hydrochloric acid and water
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. customevaporated in vacuo
  5. customthe solid residue was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-a8aaefab581a4b5ba6eee3801613b6fe
Source dataset
uspto-grants-1997_01
Patent number
US05594135

Reaction notes

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