Triethylamine → benzyl 4-(3-cyanophenoxy)-3-(3R)-[4-(pyrrolidine-1-carbonyl)benzoylamino]butyrate

HRID 747784Notes

Reaction equation

HRID 747784 reaction equation
Cl.[NH2:2][C@@H:3]([CH2:15][O:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23]#[N:24])[CH:18]=1)[CH2:4][C:5]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6].ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.C(N(CC)CC)C.[N:54]1([C:59]([C:61]2[CH:69]=[CH:68][C:64]([C:65](O)=[O:66])=[CH:63][CH:62]=2)=[O:60])[CH2:58][CH2:57][CH2:56][CH2:55]1>ClCCl>[C:23]([C:19]1[CH:18]=[C:17]([CH:22]=[CH:21][CH:20]=1)[O:16][CH2:15][C@H:3]([NH:2][C:65](=[O:66])[C:64]1[CH:63]=[CH:62][C:61]([C:59]([N:54]2[CH2:58][CH2:57][CH2:56][CH2:55]2)=[O:60])=[CH:69][CH:68]=1)[CH2:4][C:5]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6])#[N:24]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10932939Benzoic acid, 4-(1-pyrrolidinylcarbonyl)-HCID 86760704benzyl (3R)-3-amino-4-(3-cyanophenoxy)butyrate hydrochloride

Product 1

HCID 68832164benzyl 4-(3-cyanophenoxy)-3-(3R)-[4-(pyrrolidine-1-carbonyl)benzoylamino]butyrate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.8 g (5.2 mmol) of benzyl (3R)-3-amino-4-(3-cyanophenoxy)butyrate hydrochloride (the compound in step 2 in Example 52), 703 mg (5.2 mmol) of 1-hydroxybenzotriazole (hydrate), 997 mg (5.2 mmol) of 1-(3-dimethylaminopropyl)-3-ethyl carbodiimide hydrochloride, 526 mg (5.2 mmol) of triethylamine, and 1.14 g (5.2 mmol) of 4-(1-pyrrolidyl carbonyl)benzoic acid were stirred in dichloromethane overnight. The reaction solution was washed with 1 N hydrochloric acid, 1 N aqueous sodium hydroxide and saturated saline and dried over sulfate magnesium anhydride, and the solvent was distilled off. The resulting residue was purified by silica gel chromatography (ethyl acetate) to obtain the title compound.

Workup

  1. washThe reaction solution was washed with 1 N hydrochloric acid, 1 N aqueous sodium hydroxide and saturated saline
  2. dry with materialdried over sulfate magnesium anhydride
  3. distillationthe solvent was distilled off
  4. customThe resulting residue was purified by silica gel chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-bf80ac5879e1489fa5675e869d7f03b5
Source dataset
uspto-grants-2008_07
Patent number
US07396844B1

Reaction notes

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