Methanol → HCID 68618413, compound

HRID 1893706Notes

Reaction equation

HRID 1893706 reaction equation
C[O:2][C:3]([C:5]12[CH2:23][CH:22]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH:14]([NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C:13](=[O:32])[N:12]1[CH:8]([CH2:9][CH:10]([O:33][C:34]([N:36]3[CH2:44][C:43]4[C:38](=[CH:39][CH:40]=[CH:41][C:42]=4[F:45])[CH2:37]3)=[O:35])[CH2:11]1)[C:7](=[O:46])[NH:6]2)=[O:4].C1COCC1.CO.[OH-].[Li+]>CCOC(C)=O.O>[C:28]([O:27][C:25]([NH:24][CH:14]1[C:13](=[O:32])[N:12]2[CH:8]([CH2:9][CH:10]([O:33][C:34]([N:36]3[CH2:44][C:43]4[C:38](=[CH:39][CH:40]=[CH:41][C:42]=4[F:45])[CH2:37]3)=[O:35])[CH2:11]2)[C:7](=[O:46])[NH:6][C:5]2([C:3]([OH:4])=[O:2])[CH:22]([CH2:23]2)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)=[O:26])([CH3:31])([CH3:29])[CH3:30]

Participants

7

Reactant 4

HCID 887MethanolHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 68618323HCID 68618323, compound

Product 1

HCID 68618413HCID 68618413, compoundYield 97.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 14-tert-butoxycarbonylamino-18-(4-fluoro-1,3-dihydro-isoindole-2-carbonyloxy)-2,15-dioxo-3,16-diaza-tricyclo[14.3.0.04,6]nonadecane-4-carboxylic acid methyl ester (319 mg, 0.49 mmol) in a 1:1:1 mixture of THF:MeOH:H2O (6 mL) was added lithium hydroxide (104 mg, 2.47 mmol). The resulting slurry was stirred at room temperature overnight then diluted with EtOAc and washed with 1N HCl and brine. The resulting organic layer was dried over sodium sulfate and concentrated to provide the crude 14-tert-butoxycarbonylamino-18-(4-fluoro-1,3-dihydro-isoindole-2-carbonyloxy)-2,15-dioxo-3,16-diaza-tricyclo[14.3.0.04,6]nonadecane-4-carboxylic acid (300 mg, 97% yield). LCMS found 630.8 [M+H]+.

Workup

  1. washwashed with 1N HCl and brine
  2. dry with materialThe resulting organic layer was dried over sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-2a2a69da749244e8ba2a01491c83c90c
Source dataset
uspto-grants-2013_08
Patent number
US08513186B2

Reaction notes

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