Morpholine → HCID 57237740, compound

HRID 234235Notes

Reaction equation

HRID 234235 reaction equation
C[Si](C)(C(C)(C)C(C)C)[O:3][C:4]1[C:21]2[CH2:20][S:19][CH2:18][C@@H:17]([C:22]3[O:26][N:25]=[C:24]([CH3:27])[N:23]=3)[NH:16][C:15](=[S:28])[CH2:14][CH2:13][C@@H:12]([CH2:29]OS(C)(=O)=O)[CH2:11][O:10][C:9](=[O:35])[C:8]=2[C:7]([CH3:36])=[C:6]([O:37][CH3:38])[CH:5]=1.[NH:46]1[CH2:51][CH2:50][O:49][CH2:48][CH2:47]1>CO>[OH:3][C:4]1[C:21]2[CH2:20][S:19][CH2:18][C@@H:17]([C:22]3[O:26][N:25]=[C:24]([CH3:27])[N:23]=3)[NH:16][C:15](=[S:28])[CH2:14][CH2:13][C@@H:12]([CH2:29][N:46]3[CH2:51][CH2:50][O:49][CH2:48][CH2:47]3)[CH2:11][O:10][C:9](=[O:35])[C:8]=2[C:7]([CH3:36])=[C:6]([O:37][CH3:38])[CH:5]=1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 53664226HCID 53664226, compound

Product 1

HCID 57237740HCID 57237740, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

A solution of 46 mg of (4R,9R)-16-[dimethyl-(1,1,2-trimethylpropyl)silanyloxy]-14-methoxy-13-methyl-4-(3-methyl[1,2,4]oxadiazol-5-yl)-9-(methylsulfonyloxymethyl)-6-thioxo-1,3,4,5,6,7,8,9,10,12-decahydro-11,2,5-benzoxathiaazacyclotetradecin-12-one in a mixture of 0.25 ml of morpholine and 0.25 ml of methanol was stirred at 20° C. for 18 h. The solution was evaporated in vacuo and the residue was treated with ammonium fluoride in methanol in an analogous manner to the procedure described in Example 1 to yield 12 mg of (4R,9S)-16-hydroxy-14-methoxy-13-methyl-4-(3-methyl-1,2,4-oxadiazol-5-yl)-9-(morpholin-4-ylmethyl)-6-thioxo-1,3,4,5,6,7,8,9,10,12-decahydro-11,2,5-benzoxathiaazacyclotetradecin-12-one as a white solid.

Workup

  1. customThe solution was evaporated in vacuo
  2. additionthe residue was treated with ammonium fluoride in methanol in an analogous manner to the procedure

Sources & evidence

ORD record
ord-d06dac36471f4c9c9ecc975aea65e410
Source dataset
uspto-grants-1997_01
Patent number
US05594135

Reaction notes

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