Dichloromethane → HCID 9894801, compound

HRID 1794736Notes

Reaction equation

HRID 1794736 reaction equation
C([O:5][C:6](=[O:44])[CH2:7][N:8]1[C:12](=[O:13])[CH:11]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([N:21]3[CH2:26][CH2:25][CH:24]([NH:27][CH2:28][C@H:29]([OH:42])[C:30]4[CH:35]=[CH:34][C:33]([OH:36])=[C:32]([NH:37][S:38]([CH3:41])(=[O:40])=[O:39])[CH:31]=4)[CH2:23][CH2:22]3)=[CH:17][CH:16]=2)[S:10][C:9]1=[O:43])(C)(C)C.ClCCl.FC(F)(F)C(O)=O>C(OCC)C>[OH:42][C@H:29]([C:30]1[CH:35]=[CH:34][C:33]([OH:36])=[C:32]([NH:37][S:38]([CH3:41])(=[O:39])=[O:40])[CH:31]=1)[CH2:28][NH:27][CH:24]1[CH2:25][CH2:26][N:21]([C:18]2[CH:17]=[CH:16][C:15]([CH2:14][CH:11]3[S:10][C:9](=[O:43])[N:8]([CH2:7][C:6]([OH:44])=[O:5])[C:12]3=[O:13])=[CH:20][CH:19]=2)[CH2:22][CH2:23]1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 10168421HCID 10168421, compound

Product 1

HCID 9894801HCID 9894801, compoundYield 69.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 5-[[4-[4-[[(R)-2-hydroxy-2-[4-hydroxy-3-[(methylsulfonyl)amino]-phenyl]ethyl]amino]-1-piperidinyl]phenyl]methyl]-2,4-dioxo-3-thiazolidineacetic acid tert-butyl-ester (300 mg, 0.46 mmol) (which was obtained in Example 64), dichloromethane (5 mL), and trifluoroacetic acid (0.5 mL) was stirred at room temperature for 10 hours. The mixture was then poured into ethyl ether (50 mL), and the precipitated solid was filtered and dried to give an off-white solid (189 mg, 58% yield); mp 158–160° C.; 1H NMR (400 MHz, DMSO-d6) δ 1.58–1.66 (m, 2H), 2.02–2.10 (m, 2H), 2.60–2.64 (m, 2H), 2.85–3.04 (m, 4H), 3.16–3.40 (m, 4H), 3.80 (m, 2H), 4.20 (s, 2H), 4.80 (m, 1H), 5.06 (m, 1H), 6.17 (brs, 1H), 6.87–6.91 (m, 3H), 7.05–7.1 (m, 3H), 7.23 (m, 1H), 8.60 (brs, 1H), 8.80 (s, 1H), 9.94 (s, 1H), 13.3 (brs, 1H); MS (ES) m/z: 649 (MH+).

Workup

  1. filtrationthe precipitated solid was filtered
  2. customdried

Sources & evidence

ORD record
ord-9eca694380134439ad688b6f958ce916
Source dataset
uspto-grants-2006_04
Patent number
US07022716B2

Reaction notes

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