1-Hydroxybenzotriazole → HCID 22461188, compound

HRID 1937445Notes

Reaction equation

HRID 1937445 reaction equation
[C:1]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=O)=[C:7]([O:14][CH3:15])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.[NH2:38][C:39]1[CH:40]=[C:41]([CH:45]2[CH2:49][CH2:48][CH2:47][N:46]2[C:50]([O:52][C:53]([CH3:56])([CH3:55])[CH3:54])=[O:51])[CH:42]=[CH:43][CH:44]=1>CN(C=O)C.O>[C:1]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([NH:38][C:39]2[CH:40]=[C:41]([CH:45]3[CH2:49][CH2:48][CH2:47][N:46]3[C:50]([O:52][C:53]([CH3:56])([CH3:55])[CH3:54])=[O:51])[CH:42]=[CH:43][CH:44]=2)=[O:11])=[C:7]([O:14][CH3:15])[CH:6]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 126137394-tert-Butyl-2-methoxybenzoic acidHCID 22461189HCID 22461189, compound

Product 1

HCID 22461188HCID 22461188, compoundYield 34.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-tert-butyl-2-methoxy-benzoic acid (0.05 g) in DMF (1.5 mL) at room temperature, was added in order, 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (0.046 g), 1-hydroxy-benzotriazole (0.033 g) and 15 min. later, (±)-2-(3-aminophenyl)-1-(tert-butyloxycarbonyl)-pyrrolidine (0.05 g). The reaction mixture was allowed to stir for 17 h and then poured into water. The aqueous mixture was extracted with ethyl acetate twice. The combined organic layer was washed with brine, dried (sodium sulfate) and evaporated in vacuo to afford an amber oil. Suction silica gel chromatography eluting with ethyl acetate in hexane (from 30% to 100%, in 10% increments) gave desired product as an amber solid (0.03 g).

Workup

  1. extractionThe aqueous mixture was extracted with ethyl acetate twice
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried (sodium sulfate)
  4. customevaporated in vacuo
  5. customto afford an amber oil
  6. washSuction silica gel chromatography eluting with ethyl acetate in hexane (from 30% to 100%, in 10% increments)

Sources & evidence

ORD record
ord-2a7448754bd9482087dcd591c53efaba
Source dataset
uspto-grants-2002_05
Patent number
US06395759B1

Reaction notes

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