Trifluoroacetic acid → HCID 44601159, compound

HRID 882761Notes

Reaction equation

HRID 882761 reaction equation
C(OC([N:8]1[CH2:12][C@@H:11]([O:13][C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)[CH2:10][C@H:9]1[C:21]([N:23]1[CH2:29][CH2:28][CH2:27][N:26]([CH:30]2[CH2:33][CH2:32][CH2:31]2)[CH2:25][CH2:24]1)=[O:22])=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[CH:30]1([N:26]2[CH2:27][CH2:28][CH2:29][N:23]([C:21]([C@@H:9]3[CH2:10][C@H:11]([O:13][C:14]4[CH:15]=[CH:16][C:17]([F:20])=[CH:18][CH:19]=4)[CH2:12][NH:8]3)=[O:22])[CH2:24][CH2:25]2)[CH2:31][CH2:32][CH2:33]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 44600363HCID 44600363, compound

Product 1

HCID 44601159HCID 44601159, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2S,4S)-2-(4-cyclobutyl-[1,4]diazepane-1-carbonyl)-4-(4-fluoro-phenoxy)-pyrrolidine-1-carboxylic acid tert-butyl ester (969 mg, 2.09 mmol) in CH2Cl2 (5 mL) was added trifluoroacetic acid (2 mL). After 1 h, the mixture was concentrated and the residue purified by FCC to give the desired product (665 mg, 88%). MS (ESI): mass calcd. for C20H28FN3O2, 361.22; m/z found, 362.5 [M+H]+. 1H NMR (CDCl3): 6.95-6.90 (m, 2H), 6.78 (dd, J=9.0, 4.3 Hz, 2H), 4.79-4.74 (m, 1H), 3.88 (ddd, J=9.1, 6.3, 6.3 Hz, 1H), 3.81-3.69 (m, 1H), 3.58-3.47 (m, 2H), 3.47-3.37 (m, 2H), 3.08-2.76 (m, 3H), 2.59-2.28 (m, 5H), 2.00 (dd, J=16.1, 7.7 Hz, 2H), 1.95-1.72 (m, 5H), 1.69-1.53 (m, 2H).

Workup

  1. concentrationthe mixture was concentrated
  2. customthe residue purified by FCC

Sources & evidence

ORD record
ord-90fe530951624340b8f4932a8eeef347
Source dataset
uspto-grants-2012_08
Patent number
US08236792B2

Reaction notes

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