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N-Phenylanthranilic Acid → (S)-1-[2-(Phenylamino)benzoyl]-2-pyrrolidinemethanol

HRID 1457337
Notes
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Reaction equation

HRID 1457337 reaction equation
[C:1]1([NH:7][C:8]2[C:9](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:10]([OH:12])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.ON1C2C=CC=CC=2N=N1.[NH:28]1[CH2:34][CH2:33][CH2:32][C@H:29]1[CH2:30][OH:31].C1CCC(N=C=NC2CCCCC2)CC1>CN(C=O)C.C(Cl)Cl>[C:1]1([NH:7][C:8]2[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=2[C:10]([N:28]2[CH2:34][CH2:33][CH2:32][C@H:29]2[CH2:30][OH:31])=[O:12])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1
ParticipantsProcedureSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 4386N-Phenylanthranilic AcidHCID 10868DicyclohexylcarbodiimideHCID 640091L-ProlinolHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 54043507(S)-1-[2-(Phenylamino)benzoyl]-2-pyrrolidinemethanol

Reagents, catalysts & solvents 2

HCID 6228
Dimethylformamide
Solvent
HCID 6344DichloromethaneSolvent

Procedure

2.13 g (10 mmol) of N-phenylanthranilic acid, 1.35 g (10 mmol) of 1-hydroxybenzotriazole hydrate, 1.0 ml (10 mmol) of L-prolinol and 2.06 g (10 mmol) of DCC in 50 ml 1:1/methylene chloride:DMF. The coupling was carried out as described in Example 25 for the coupling of the acid and S(+)-2-pyrrolidinemethanol. Clean product of the title compound was obtained in virtually quantitative yield as a brownish gum without chromatographic purification. TLC (90:10/CH2Cl2 :MeOH): Rf =0.75. 1H NMR (CDCl3) δ: 7.50(bs,1H); 6.75-7.36 (m,9H); 4.65-4.80(m,1H); 4.25-4.40 (m,1H); 3.38-3.85(m,4H); 1.55-2.15(m,4H).

Sources & evidence

ORD record
ord-ee703810dde54d1c8d23cecf9efc738d
Source dataset
uspto-grants-1998_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05847155

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes