Trifluoroacetic acid → Benzoic acid,4-[(1s)-1-[[(2,3-dihydro-1h-indol-7-yl)carbonyl]amino]ethyl]-,methyl ester

HRID 646181Notes

Reaction equation

HRID 646181 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C@@H:11]([NH:13][C:14]([C:16]2[CH:17]=[CH:18][CH:19]=[C:20]3[C:24]=2[N:23](C(OC(C)(C)C)=O)[CH2:22][CH2:21]3)=[O:15])[CH3:12])=[CH:7][CH:6]=1)=[O:4].C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:23]1[C:24]2[C:20](=[CH:19][CH:18]=[CH:17][C:16]=2[C:14]([NH:13][C@H:11]([C:8]2[CH:7]=[CH:6][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:10][CH:9]=2)[CH3:12])=[O:15])[CH2:21][CH2:22]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58125255tert-butyl 7-({(1S)-1-[4-(methoxycarbonyl)phenyl]ethyl}carbamoyl)indoline-1-carboxylate

Product 1

HCID 59264925Benzoic acid,4-[(1s)-1-[[(2,3-dihydro-1h-indol-7-yl)carbonyl]amino]ethyl]-,methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-butyl 7-[({(1S)-1-[4-(methoxycarbonyl)phenyl]ethyl}amino)carbonyl]indoline-1-carboxylate (510 mg, 1.2 mmol) was dissolved in CH2Cl2 (5 ml) and TFA (5 ml) was added, the solution was stirred for 1 hour. The solvent was removed. NaHCO3 (sat.) was added and extracted 3× with EtOAc. The combined organic layers were washed with water and brine, then dried over MgSO4. 1H NMR (500 MHz, DMSO-d6): δ 8.50 (d, 1H), 7.90 (d, 2H), 7.55 (m, 3H), 7.10 (d, 1H), 6.50 (m, 2H), 5.15 (m, 1H), 3.85 (s, 3H), 3.50 (m, 2H), 2.90 (m, 2H), 1.40 (d, 3H).

Workup

  1. customThe solvent was removed
  2. additionNaHCO3 (sat.) was added
  3. extractionextracted 3× with EtOAc
  4. washThe combined organic layers were washed with water and brine
  5. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-e21b7c62c8b8414eb9f49357c99760ba
Source dataset
uspto-grants-2010_04
Patent number
US07705035B2

Reaction notes

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