Methanol → HCID 68795508, compound

HRID 1893704Notes

Reaction equation

HRID 1893704 reaction equation
C[O:2][C:3]([C:5]12[CH2:23][CH:22]1[CH:21]=[CH: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)[CH:21]=[CH: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 68615924HCID 68615924, compound

Product 1

HCID 68795508HCID 68795508, compoundYield 101.2%

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]nonadec-7-ene-4-carboxylic acid methyl ester (916 mg, 1.43 mmol) in a 1:1:1 mixture of THF:MeOH:H2O (12 mL) was added lithium hydroxide (299 mg, 41.96 mmol). The resulting slurry was stirred at room temperature overnight then diluted with EtOAc and washed with 1 N 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]nonadec-7-ene-4-carboxylic acid (910 mg, 100% yield). LCMS found 628.8 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-fd1abdd40cf94c2b8fbc561fdab9ac95
Source dataset
uspto-grants-2013_08
Patent number
US08513186B2

Reaction notes

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