Trifluoroacetic acid → HCID 10283272, compound

HRID 1278774Notes

Reaction equation

HRID 1278774 reaction equation
[F:1][C:2]1[CH:48]=[CH:47][C:46]([F:49])=[CH:45][C:3]=1[CH2:4][N:5]([S:14]([C:17]1[CH:22]=[CH:21][C:20]([N:23]2[CH2:28][CH2:27][CH:26]([NH:29][CH2:30][C@H:31]([OH:44])[C:32]3[CH:37]=[CH:36][C:35]([OH:38])=[C:34]([NH:39][S:40]([CH3:43])(=[O:42])=[O:41])[CH:33]=3)[CH2:25][CH2:24]2)=[CH:19][CH:18]=1)(=[O:16])=[O:15])[CH2:6][C:7]([O:9]C(C)(C)C)=[O:8].C(O)(C(F)(F)F)=O>O>[F:1][C:2]1[CH:48]=[CH:47][C:46]([F:49])=[CH:45][C:3]=1[CH2:4][N:5]([S:14]([C:17]1[CH:18]=[CH:19][C:20]([N:23]2[CH2:24][CH2:25][CH:26]([NH:29][CH2:30][C@H:31]([OH:44])[C:32]3[CH:37]=[CH:36][C:35]([OH:38])=[C:34]([NH:39][S:40]([CH3:43])(=[O:41])=[O:42])[CH:33]=3)[CH2:27][CH2:28]2)=[CH:21][CH:22]=1)(=[O:15])=[O:16])[CH2:6][C:7]([OH:9])=[O:8]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 10305737HCID 10305737, compound

Product 1

HCID 10283272HCID 10283272, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

This compound was prepared from tert-butyl 2-{(2,5-difluorobenzyl)[(4-{4-[((2R)-2-hydroxy-2-{4-hydroxy-3-[(methylsulfonyl)amino]phenyl}ethyl)amino]-1-piperidinyl}phenyl)sulfonyl]amino}acetate in substantially the same manner, as described in Example 53, with one change; the mixture was stirred at room temperature for 20 hours. The volatiles were removed and the product was purified by reverse phase chromatography to give a white solid (1.44 9, 42% yield): mp 80-82° C.; MS m/e 669 (M+H)+; 1H NMR (DMSO-d6 400 MHz) 81.62 (m, 2H), 2.11 (m, 2H), 2.85 (m, 2H), 2.94 (s, 3H), 2.96 (m, 1H), 3.11 (m, 1H), 3.34 (m, 1H), 3.88 (s, 2H), 3.99 (m, 2H), 4.37 (s, 2H), 4.79 (m, 1H), 6.01 (br, 1H), 6.90 (d, 1H), 7.05 (m, 3H), 7.18 (m, 3H), 7.21 (s, 1H), 7.59 (d, 2H), 8.58 (brs, 1H), 8.66 (brs, 1H), 8.74 (brs, 1H), 10.01 (brs, 1H); Analysis for C29H34F2N4O8S2×2.0 CF3COOH×0.73 H2O Calc'd: C, 43.52; H, 4.11 ; N, 6.15 Found: C, 42.95; H, 3.93; N, 6.08.

Workup

  1. customThe volatiles were removed
  2. customthe product was purified by reverse phase chromatography
  3. customto give a white solid (1.44 9, 42% yield)

Sources & evidence

ORD record
ord-45a89b3fd082497195c3438456f36fc5
Source dataset
uspto-grants-2002_09
Patent number
US06444685B1

Reaction notes

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