Methanol → HCID 67050798, compound

HRID 1498152Notes

Reaction equation

HRID 1498152 reaction equation
[N:1]1[N:5]2[C:6]3[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=3[O:8][CH2:9][CH2:10][C:4]2=[N:3][C:2]=1[C:15]([O:17]C)=[O:16].CO.O.[OH-].[Li+]>C1COCC1>[N:1]1[N:5]2[C:6]3[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=3[O:8][CH2:9][CH2:10][C:4]2=[N:3][C:2]=1[C:15]([OH:17])=[O:16]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 3939Lithium HydroxideHCID 67050638HCID 67050638, compound

Product 1

HCID 67050798HCID 67050798, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

Ester 86 (0.166 g, 0.677 mmol) was dissolved in 3:2:1 THF:MeOH:H2O (31.2 mL), treated with 4 N aqueous lithium hydroxide (1.32 mL), and the mixture was stirred for 30 min at 25° C. (FIG. 18). The reaction was quenched with 1 N aq. HCl (20 mL) and the solution was extracted three times with 20 mL EtOAc. The combined organic extracts were dried with sodium sulfate, and concentrated to give crude 4,5-dihydrobenzo[b][1,2,4]triazolo[1,5-d][1,4]oxazepine-2-carboxylic acid which was taken forward to the next step. LRMS m/z Calcd. for C12H9N3O3: 231.06439. found: 232.1 [M+1].

Workup

  1. customThe reaction was quenched with 1 N aq. HCl (20 mL)
  2. extractionthe solution was extracted three times with 20 mL EtOAc
  3. dry with materialThe combined organic extracts were dried with sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-6bb5db27c54643caa1ffe5a47980b703
Source dataset
uspto-grants-2015_12
Patent number
US09198918B2

Reaction notes

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