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Dicyclohexylcarbodiimide → Phenyl-phenylamino-acetic acid 1-methyl-azepan-4-yl ester

HRID 77029
Notes
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Reaction equation

HRID 77029 reaction equation
[C:1]1([CH:7]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:8]([OH:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1CCC(N=[C:25]=[N:26][CH:27]2[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)CC1.C1C=CC2N(O)N=NC=2C=1.CN1CCCC(O)CC1>C1COCC1>[CH3:25][N:26]1[CH2:27][CH2:32][CH2:31][CH:30]([O:9][C:8](=[O:10])[CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:29][CH2:28]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 19375alpha-(Phenylamino)benzeneacetic acidHCID 757711-HydroxybenzotriazoleHCID 109755091-Methylazepan-4-ol

Product 1

HCID 59401250Phenyl-phenylamino-acetic acid 1-methyl-azepan-4-yl esterYield 20.3%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

A mixture of 2-phenyl-2-(phenylamino)acetic acid (I1) (175 mg, 0.77 mmol), DCC (192 mg, 0.92 mmol), HOBt (124 mg, 0.92 mmol) and 1-methyl-azepan-4-ol (100 mg, 0.77 mmol) in dry THF (100 mL) is stirred at RT overnight under nitrogen flowstream (UPLC-MS monitoring: complete conversion). The solvent is evaporated and the residue is taken up with aq. HCl and washed with EtOAc. The aqueous phase is basified with NaHCO3 and extracted with DCM (three times). The organic layers are combined, dried over Na2SO4, filtered and evaporated to dryness. The resulting crude is first purified by flash chromatography (DCM to DCM/MeOH=95/5) and then by preparative LC-MS. The purified compound is partitioned between sat. NaHCO3 and DCM, the organic phase is dried over Na2SO4, filtered and evaporated under vacuum to give 53 mg of the title compound as brown oil (20% yield, mixture of diastereoisomers).

Workup

  1. customThe solvent is evaporated
  2. washwashed with EtOAc
  3. extractionextracted with DCM (three times)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe resulting crude is first purified by flash chromatography (DCM to DCM/MeOH=95/5)
  8. customThe purified compound is partitioned between sat. NaHCO3 and DCM
  9. dry with materialthe organic phase is dried over Na2SO4
  10. filtrationfiltered
  11. customevaporated under vacuum

Sources & evidence

ORD record
ord-0605cbee109747b89d917af46f3abb88
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08835682B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes