Trifluoroacetic acid → HCID 67975417, compound

HRID 1844098Notes

Reaction equation

HRID 1844098 reaction equation
C(OC([N:8]1[C:12](=[O:13])/[C:11](=[CH:14]\[OH:15])/[CH:10]2[CH2:16][C:17]3[C:22]([CH:9]12)=[CH:21][CH:20]=[CH:19][CH:18]=3)=O)(C)(C)C.FC(F)(F)C(O)=O.[Na]>ClCCl>[OH:15]/[CH:14]=[C:11]1/[CH:10]2[CH2:16][C:17]3[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:9]2[NH:8][C:12]/1=[O:13]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 5360545SodiumHCID 67975730HCID 67975730, compound

Product 1

HCID 67975417HCID 67975417, compoundYield 102%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 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 (0.400 g, 1.32 mmol) in dichloromethane (20 mL) was added trifluoroacetic acid (2 mL) at 0° C. The solution was stirred for 1 h. A saturated solution of sodium hydrogenocarbonate was added and the aqueous layer was extracted with dichloromethane. The combined organic layers were washed with a saturated solution of sodium hydrogenocarbonate, dried and concentrated in vacuo to give 3-[1-Hydroxy-meth-(Z)-ylidene]-3,3a,4,8b-tetrahydro-1H-indeno[1,2-b]pyrrol-2-one C1 (White solid, 271 mg, quant.). C12H11NO2; MW: 201.23; LCMS (method A) RT 1.18 min; ES: 256 (MH++MeCN), 224 (MNa+), 202 (MH+); IR: 3264, 1678 cm−1; 1H NMR (400 MHz, DMSO-d6) δ 10.00 (1H, s), 7.16-7.38 (4H, m), 7.13 (1H, d), 4.94 (1H, d), 3.68-3.82 (1H, m), 3.31 (2H, dd), 3.01 (1H, dd) ppm.

Workup

  1. extractionthe aqueous layer was extracted with dichloromethane
  2. washThe combined organic layers were washed with a saturated solution of sodium hydrogenocarbonate
  3. customdried
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-310d7982ab4b4144a4cbc385ba37c3c7
Source dataset
uspto-grants-2015_02
Patent number
US08946280B2

Reaction notes

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