Acetic Acid → HCID 89590959, compound

HRID 522409Notes

Reaction equation

HRID 522409 reaction equation
[CH3:1][C:2]1([C@H:8]2[C:42](=[O:43])[N:41]3[CH2:44][C@@H:38]([CH2:39][C@H:40]3[C:45]([O:47]C)=[O:46])[O:37][C:20]3=[N:21][C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][C:27]=4[C:28]([O:29][CH:30]4[CH2:35][CH2:34][N:33]([CH3:36])[CH2:32][CH2:31]4)=[C:19]3[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][C@@H:13]3[CH2:49][C@H:12]3[O:11][C:10](=[O:50])[NH:9]2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.O.[OH-].[Li+].CO.C(O)(=O)C>O.C1COCC1>[CH3:1][C:2]1([C@H:8]2[C:42](=[O:43])[N:41]3[CH2:44][C@@H:38]([CH2:39][C@H:40]3[C:45]([OH:47])=[O:46])[O:37][C:20]3=[N:21][C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][C:27]=4[C:28]([O:29][CH:30]4[CH2:35][CH2:34][N:33]([CH3:36])[CH2:32][CH2:31]4)=[C:19]3[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][C@@H:13]3[CH2:49][C@H:12]3[O:11][C:10](=[O:50])[NH:9]2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 887MethanolHCID 168937Lithium hydroxide, monohydrateHCID 89590849HCID 89590849, compound

Product 1

HCID 89590959HCID 89590959, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A round-bottom flask was charged with the product of step 6 (450 mg, 0.651 mmol) and lithium hydroxide monohydrate (137 mg, 3.26 mmol). MeOH (2171 μl), THF (2171 μl) and water (2171 μl) were successively added and the mixture was stirred at room temperature LCMS showed complete reaction after 2 hours. The reaction was quenched by addition of acetic acid (373 μl, 6.51 mmol). Water was added (20 mL) and the mixture was extracted with dichloromethane (2×20 mL) and ethyl acetate (20 mL). The combined organic extracts were dried over magnesium sulfate, filtered and concentrated in rotavap. Residual acetic acid was azeotropically removed with toluene to give the title compound as a crude product (450 mg, 0.665 mmol, 102% yield) as a white powder. No further purification was carried out.

Workup

  1. customreaction after 2 hours
  2. extractionthe mixture was extracted with dichloromethane (2×20 mL) and ethyl acetate (20 mL)
  3. dry with materialThe combined organic extracts were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in rotavap
  6. customResidual acetic acid was azeotropically removed with toluene

Sources & evidence

ORD record
ord-dd7659e4fd424182aa35f8c7670cf37c
Source dataset
uspto-grants-2016_05
Patent number
US09328138B2

Reaction notes

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