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Dichloromethane → HCID 21077916, compound

HRID 1375073
Notes
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Reaction equation

HRID 1375073 reaction equation
C([O:5][C:6](=[O:43])[CH2:7][C:8]1([C:13]2[CH:18]=[CH:17][C:16]([N:19]([C:21](=[O:42])[CH2:22][C:23]3[CH:28]=[CH:27][C:26]([NH:29][C:30]([NH:32][C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=4[CH3:39])=[O:31])=[C:25]([O:40][CH3:41])[CH:24]=3)[CH3:20])=[CH:15][CH:14]=2)[CH2:12][CH2:11][CH2:10][CH2:9]1)(C)(C)C.FC(F)(F)C(O)=O.ClCCl>O>[CH3:41][O:40][C:25]1[CH:24]=[C:23]([CH2:22][C:21]([N:19]([CH3:20])[C:16]2[CH:17]=[CH:18][C:13]([C:8]3([CH2:7][C:6]([OH:43])=[O:5])[CH2:12][CH2:11][CH2:10][CH2:9]3)=[CH:14][CH:15]=2)=[O:42])[CH:28]=[CH:27][C:26]=1[NH:29][C:30]([NH:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[CH3:39])=[O:31]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 69420098[1-{4-[{2-[3-Methoxy-4-[3-o-tolyl-ureido]-phenyl]-acetyl}-methyl-amino]-phenyl}-cyclopentyl]-acetic acid tert-butyl ester

Product 1

HCID 21077916HCID 21077916, compoundYield 79.9%

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Procedure

[1-{4-[{2-[3-Methoxy-4-[3-o-tolyl-ureido]-phenyl]-acetyl}-methyl-amino]-phenyl}-cyclopentyl]-acetic acid tert-butyl ester [0.18 g, Reference Example 8(b)] was treated with a mixture of trifluoroacetic acid (6 mL), dichloromethane (1.2 mL) and water (0.75 mL)and the resulting solution was then stirred at room temperature, under argon, for 1.5 hours. The amber coloured reaction mixture was evaporated and the residue was chased twice with toluene (20 mL) to yield an amber gum. This gum was triturated with pentane and the solid obtained was washed with pentane and then dried at 60° C., under vacuum, to give the title compound (0.13 g) as a pale yellow solid, m.p. softens at 100° C. then slowly melts from 118–150° C.

Workup

  1. customreaction mixture
  2. customwas evaporated
  3. customto yield an amber gum
  4. customThis gum was triturated with pentane
  5. customthe solid obtained
  6. washwas washed with pentane
  7. customdried at 60° C., under vacuum

Sources & evidence

ORD record
ord-b4fd66bc22854bfa9c53814ede105903
Source dataset
uspto-grants-2007_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07166616B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes