Hydrochloric Acid → HCID 67975730, compound

HRID 1844096Notes

Reaction equation

HRID 1844096 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:12](=[O:13])/[C:11](=[CH:14]\N(C)C)/[CH:10]2[CH2:18][C:19]3[C:24]([CH:9]12)=[CH:23][CH:22]=[CH:21][CH:20]=3)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[O:26]1CCCC1>C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[C:12](=[O:13])/[C:11](=[CH:14]\[OH:26])/[CH:10]2[CH2:18][C:19]3[C:24]([CH:9]12)=[CH:23][CH:22]=[CH:21][CH:20]=3)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 67975561HCID 67975561, compound

Product 1

HCID 67975730HCID 67975730, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-[1-dimethylamino-meth-(Z)-ylidene]-2-oxo-3,3a,4,8b-tetrahydro-2H-indeno[1,2-b]pyrrole-1-carboxylic acid tert-butyl ester E1 (190 mg, 0.579 mmol) in tetrahydrofurane (2 mL) was added hydrogen chloride (1M, 0.87 mL). The solution was stirred at room temperature for 3 h. The solution was diluted with ethyl acetate and washed with water, brine, dried and concentrated. The residue was triturated with ethyl acetate to give 3-[1-Hydroxy-meth-(Z)-ylidene]-2-oxo-3,3a,4,8b-tetrahydro-2H-indeno[1,2-b]pyrrole-1-carboxylic acid tert-butyl ester D1 (White powder, 140 mg, 80%). C17H19NO4; MW: 301.35; LCMS (method A) RT 1.72 min; ES: 302 (MK), 246; 1H NMR (400 MHz, DMSO-d6) δ 11.04 (1H, s), 7.54 (1H, d), 7.42 (1H, d), 7.13-7.31 (3H, m), 5.59 (1H, d), 3.70 (1H, m), 3.22 (1H, dd), 3.15 (1H, dd), 1.53 (10H, s) ppm.

Workup

  1. washwashed with water, brine
  2. customdried
  3. concentrationconcentrated
  4. customThe residue was triturated with ethyl acetate

Sources & evidence

ORD record
ord-3a7136c4f3c3450eaf0e4a017b6c388a
Source dataset
uspto-grants-2015_02
Patent number
US08946280B2

Reaction notes

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