Trifluoroacetic acid → HCID 59784095, compound

HRID 2079761Notes

Reaction equation

HRID 2079761 reaction equation
C(OC([NH:8][C@@H:9]([CH:41]([CH3:43])[CH3:42])[C:10]([N:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])[CH2:14][C@H:13]1[C:28]([NH:30][C@H:31]1[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH2:34][CH2:33][CH2:32]1)=[O:29])=[O:11])=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:8][C@@H:9]([CH:41]([CH3:43])[CH3:42])[C:10]([N:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])[CH2:14][C@H:13]1[C:28]([NH:30][C@H:31]1[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH2:34][CH2:33][CH2:32]1)=[O:29])=[O:11]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59784110HCID 59784110, compound

Product 1

HCID 59784095HCID 59784095, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound 4 (15.50 g, 26.2 mmol) is BOC-deprotected using TFA (97 mL, 1.31 mol) in CH2Cl2 (500 mL) under the same conditions as for step 2. After workup, the desired free amine 5 is obtained as an off-white foam (12.57 g, 97% yield): 1H NMR δ (CDCl3) 7.28-7.42 (m, 5H), 7.03-7.19 (m, 4H), 6.07-6.35 (br m, 1H), 5.09-5.27 (br m, 3 H), 3.68-4.81 (br m, 3H), 2.66-3.53 (br m, 6H), 1.45-2.04 (br m, 8H), 0.74-1.00 (br m, 1H); LCMS (APCl+) 493.7 (MH+, 100%).

Sources & evidence

ORD record
ord-1d0a6c4f85d547d886bfe22d7c678605
Source dataset
uspto-grants-2011_04
Patent number
US07932255B2

Reaction notes

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