Trifluoroacetic acid → Trifluoroacetic acid

HRID 660394Notes

Reaction equation

HRID 660394 reaction equation
[CH3:1][C:2]([CH3:46])([CH2:42][CH2:43][CH2:44][CH3:45])[C:3]([NH:5][CH2:6][C@@H:7]1[O:11]C(C)(C)[N:9](C(OC(C)(C)C)=O)[C@H:8]1[CH2:21][C@H:22]([CH:26]([OH:41])[C:27]1[CH:35]=[C:34]2[C:30]([CH:31]=[N:32][N:33]2[CH2:36][CH2:37][CH2:38][O:39][CH3:40])=[CH:29][CH:28]=1)[CH:23]([CH3:25])[CH3:24])=[O:4].[C:47]([OH:53])([C:49]([F:52])([F:51])[F:50])=[O:48]>C(Cl)Cl>[NH2:9][C@@H:8]([CH2:21][C@H:22]([CH:26]([OH:41])[C:27]1[CH:35]=[C:34]2[C:30]([CH:31]=[N:32][N:33]2[CH2:36][CH2:37][CH2:38][O:39][CH3:40])=[CH:29][CH:28]=1)[CH:23]([CH3:25])[CH3:24])[C@@H:7]([OH:11])[CH2:6][NH:5][C:3](=[O:4])[C:2]([CH3:1])([CH3:46])[CH2:42][CH2:43][CH2:44][CH3:45].[C:47]([OH:53])([C:49]([F:52])([F:51])[F:50])=[O:48]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59630984(4S,5S)-tert-butyl 5-((2,2-dimethylhexanamido)methyl)-4-((S)-2-(hydroxy(1-(3-methoxypropyl)-1H-indazol-6-yl)methyl)-3-methylbutyl)-2,2-dimethyloxazolidine-3-carboxylate

Product 2

HCID 6422Trifluoroacetic acidYield 42%HCID 68786312N-((2S,3S,5S)-3-amino-2-hydroxy-5-(hydroxy(1-(3-methoxypropyl)-1H-indazol-6-yl)methyl)-6-methylheptyl)-2,2-dimethylhexanamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (4S,5S)-tert-butyl 5-((2,2-dimethylhexanamido)methyl)-4-((S)-2-(hydroxy(1-(3-methoxypropyl)-1H-indazol-6-yl)methyl)-3-methylbutyl)-2,2-dimethyloxazolidine-3-carboxylate (45 mg, 0.07 mmol) in CH2Cl2 (8 mL) at 0° C. was added TFA (2 mL). The mixture was stirred for ˜1 h and concentrated. The residue was purified by preparative HPLC to give N-((2S,3S,5S)-3-amino-2-hydroxy-5-(hydroxy(1-(3-methoxypropyl)-1H-indazol-6-yl)methyl)-6-methylheptyl)-2,2-dimethylhexanamide as its TFA salt (15 mg, 42%). 1H NMR (400 MHz, CD3OD): δ 8.00 (s, 1H), 7.74 (d, J=8.4 Hz, 1H), 7.55 (m, 1H), 7.17 (m, 1H), 4.50 (m, 2H), 3.84-3.68 (m, 2H), 3.45 (m, 1H), 3.27 (s, 3H), 3.25-3.18 (m, 3H), 2.13 (m, 2H), 1.89-1.72 (m, 2H), 1.55 (m, 3H), 1.32-1.11 (m, 9H), 0.99-0.80 (m, 12H); MS: 489 (M++1).

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-d14b60f9378c4d50b315ed4b3ee861e1
Source dataset
uspto-grants-2011_12
Patent number
US08084485B2

Reaction notes

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