Trifluoroacetic acid methylene chloride → HCID 57849719, compound

HRID 737199Notes

Reaction equation

C(OC([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15](=[O:45])[C:16]2[CH:21]=[CH:20][C:19]([C:22]3[N:23]=[C:24]([NH:27][C:28]([CH:30]4[CH2:34][CH2:33][CH2:32][N:31]4[C:35]([O:37][CH2:38][C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)=[O:36])=[O:29])[S:25][CH:26]=3)=[CH:18][CH:17]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(OC(N1CCCC(NC(=O)C2C=CC(C3N=C(NC(C4CCCN4C(OCC4C=CC=CC=4)=O)=O)SC=3)=CC=2)C1)=O)(C)(C)C.C(Cl)Cl.C(O)(C(F)(F)F)=O>>[CH2:38]([O:37][C:35]([N:31]1[CH2:32][CH2:33][CH2:34][CH:30]1[C:28](=[O:29])[NH:27][C:24]1[S:25][CH:26]=[C:22]([C:19]2[CH:20]=[CH:21][C:16]([C:15](=[O:45])[NH:14][CH:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)=[CH:17][CH:18]=2)[N:23]=1)=[O:36])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1

Participants

Reactant 3

HCID 21863450Trifluoroacetic acid methylene chloride

HCID 59140916HCID 59140916, compound

HCID 59140918HCID 59140918, compound

Product 1

HCID 57849719HCID 57849719, compound

Procedure

4-(4-{2-[(1-Benzyloxycarbonyl-pyrrolidine-2-carbonyl)-amino]-thiazol-4-yl}-benzoylamino)-piperidine-1-carboxylic acid tert-butyl ester (Compound 5336 Example 336 100 mg, 0.16 mmol) was dissolved in 4 mL of 1:1 solution of CH2Cl2/TFA and stirred for 1.5 at room temperature. The reaction mixture was evaporated under reduced pressure to give pure desired product. MS: 534.2(M+H+); H1 NMR (MeOH-d4): δ(ppm) (HCl salt) 7.99 (m, 4H), 7.28 (m, 3H), 7.12 (d, 1H), 7.00 (d, 2H), 5.02 (m, 2H), 4.56 (m, 2H), 4.19 (m, 1H), 3.69 (m, 1H), 3.55 (m, 4H), 3.17 (t, 2H), 2.16 (m, 1H), 2.11 (m, 4H), 1.92 (m, 4H).

Workup

customThe reaction mixture was evaporated under reduced pressure

Sources & evidence

ORD record: ord-5f6e19381c324a8dade4551a6d6354d2
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07595398B2

Reaction notes

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