Water → HCID 67032570, compound

HRID 2167913Notes

Reaction equation

HRID 2167913 reaction equation
C([O:5][C:6](=[O:29])[CH2:7][CH2:8][N:9]1[CH2:14][CH2:13][O:12][CH:11]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:17][CH:16]=2)[CH2:10]1)(C)(C)C.[C:30]([OH:36])([C:32]([F:35])([F:34])[F:33])=[O:31].O>C(Cl)Cl>[F:33][C:32]([F:35])([F:34])[C:30]([OH:36])=[O:31].[CH2:22]([O:21][C:18]1[CH:17]=[CH:16][C:15]([CH:11]2[O:12][CH2:13][CH2:14][N:9]([CH2:8][CH2:7][C:6]([OH:29])=[O:5])[CH2:10]2)=[CH:20][CH:19]=1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 67032496HCID 67032496, compound

Product 1

HCID 67032570HCID 67032570, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The crude 3-{2-[4-(benzyloxy)-phenyl]morpholin-4-yl}-propionic acid tert-butyl ester (see §3) was treated with a mixture of TFA, water, and CH2Cl2 (30:3:67; 3 mL) and stirred at RT for 2 h. Subsequently, the volatiles were removed in vacuo, and the crude product was purified by preparative HPLC to afford 3-{2-[4-(benzyloxy)-phenyl]-morpholin-4-yl}-propionic acid trifluoroacetic acid salt; Rt=1.86 min. (System A), [M+H]+ Found: 342.19; Calc: 342.17. Conditions for the preparative LC-MS: Injection of the crude product dissolved in 600 L DMSO/CH3CN 1:2; column Waters Sunfire 19×100 mm 5 μm 45° C., mobile phase water/CH3CN/TFA 0.1% 25 mL/min, run 20 min 10%-90% CH3CN, detection with UV 210-260 nm.

Workup

  1. customSubsequently, the volatiles were removed in vacuo
  2. customthe crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-b716ee12070e4bff9575f889b6bb22a9
Source dataset
uspto-grants-2015_06
Patent number
US09045441B2

Reaction notes

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