Trifluoroacetic acid → HCID 12110932, compound

HRID 853897Notes

Reaction equation

HRID 853897 reaction equation
C(OC([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][C@H:9]1[CH2:17][O:18][CH3:19])=O)(C)(C)C.C(O)(C(F)(F)F)=O.[OH-].[Na+]>C(Cl)Cl>[CH3:19][O:18][CH2:17][C@@H:9]1[CH2:10][C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[NH:8]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium Hydroxide2×HCID 69409635HCID 69409635, compound

Product 1

HCID 12110932HCID 12110932, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (S)-2-methoxymethyl-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester (3.863 g, 4.67 mmol, 1 eq) in CH2Cl2 (50 mL) was cooled to 0° C. and TFA (12 mL) was added. The reaction was stirred at room temperature for 1 hr and then poured carefully into 1 N NaOH. The pH was adjusted to basic with 2.5 N NaOH and it was extracted with CH2Cl2. The combined organics dried over sodium sulfate and concentrated to afford the title compound as a yellow oil, which was used crude in the following reaction. NMR (400 Mz, DMSO-d6): consistent.

Workup

  1. extractionwas extracted with CH2Cl2
  2. dry with materialThe combined organics dried over sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-ab0c58afa66643cbbd0ecdfa15efdf59
Source dataset
uspto-grants-2007_08
Patent number
US07256198B2

Reaction notes

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