Trifluoroacetic acid methylene chloride → HCID 131729773, compound
Reaction equation
C([NH:8][C@@H:9]([CH2:35][C@H:36]1[CH2:41][CH2:40][CH2:39][O:38][CH2:37]1)[CH2:10][NH:11][C:12]([N:14]1[CH2:19][CH2:18][CH2:17][C@@H:16]([C@H:20]([C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([Cl:34])[CH:29]=2)[O:21][CH2:22][CH2:23][NH:24][C:25](=[O:27])[O-:26])[CH2:15]1)=[O:13])(OC(C)(C)C)=O.C(Cl)Cl.[C:45]([OH:51])([C:47]([F:50])([F:49])[F:48])=[O:46]>>[OH:51][C:45]([C:47]([F:50])([F:49])[F:48])=[O:46].[NH2:8][C@@H:9]([CH2:35][C@H:36]1[CH2:41][CH2:40][CH2:39][O:38][CH2:37]1)[CH2:10][NH:11][C:12]([N:14]1[CH2:19][CH2:18][CH2:17][C@@H:16]([C@H:20]([C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([Cl:34])[CH:29]=2)[O:21][CH2:22][CH2:23][NH:24][C:25](=[O:26])[OH:27])[CH2:15]1)=[O:13]Participants
Procedure
The 2-((R)—((R)-1-((S)-2-(Boc-amino)-3-((R)-tetrahydro-2H-pyran-3-yl)propylcarbamoyl)piperidin-3-yl)(3-chlorophenyl)methoxy)ethylcarbamate (5 mg, 0.008 mmol) was dissolved in DCM/TFA (3/1 mL). The solution was stirred for 30 min and concentrated. The crude mixture was purified on preparative HPLC to afford 2-((R)—((R)-1-((S)-2-amino-3-((R)-tetrahydro-2H-pyran-3-yl)propylcarbamoyl)piperidin-3-yl)(3-chlorophenyl)methoxy)ethylcarbamate TFA salt 2.8 mg, yield 54%. 1H NMR (CD3OD) δ 7.36-7.32 (m, 3H), 7.23 (d, J=7.6 Hz, 1H), 4.20 (br d, J=13.6 Hz, 1H), 4.04 (d, J=8.8 Hz, 1H), 3.89-3.78 (m, 3H), 3.64 (s, 3H), 3.48-3.42 (m, 2H), 3.37 (m, 1H), 3.28-3.24 (m, 5H), 3.15 (dd, J=10.8, 9.2 Hz, 1H), 2.92 (m, 2H), 1.97 (m, 1H), 1.78 (m, 2H), 1.68-1.54 (m, 4H), 1.45-1.07 (m, 5H). MS ESI+ve m/z 511 (M+H).
Workup
- concentrationconcentrated
- customThe crude mixture was purified on preparative HPLC
Sources & evidence
- ORD record
- ord-15ce5ceee95f4d82bb4ba9399cfd4f15
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08198453B2
Reaction notes
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