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Benzoic acid, 4-amino-, 1,1-dimethylethyl ester → benzyl (2S,4S)-2-[(4-{[(2-methyl-2-propanyl)oxy]carbonyl}phenyl)carbamoyl]-4-[4-(methylsulfonyl)-1-piperazinyl]-1-pyrrolidinecarboxylate

HRID 1053812
Notes
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Reaction equation

HRID 1053812 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C@@H:14]([N:16]2[CH2:21][CH2:20][N:19]([S:22]([CH3:25])(=[O:24])=[O:23])[CH2:18][CH2:17]2)[CH2:13][C@H:12]1[C:26](O)=[O:27])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:29][C:30]1[CH:42]=[CH:41][C:33]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])=[CH:32][CH:31]=1>N1C=CC=CC=1>[CH3:40][C:37]([O:36][C:34]([C:33]1[CH:41]=[CH:42][C:30]([NH:29][C:26]([C@@H:12]2[CH2:13][C@H:14]([N:16]3[CH2:21][CH2:20][N:19]([S:22]([CH3:25])(=[O:24])=[O:23])[CH2:18][CH2:17]3)[CH2:15][N:11]2[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:10])=[O:27])=[CH:31][CH:32]=1)=[O:35])([CH3:38])[CH3:39]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 233272Benzoic acid, 4-amino-, 1,1-dimethylethyl esterHCID 118107654(2S,4S)-1-[(benzyloxy)carbonyl]-4-[4-(methylsulfonyl)-1-piperazinyl]-2-pyrrolidinecarboxylic acid

Product 1

HCID 122584929benzyl (2S,4S)-2-[(4-{[(2-methyl-2-propanyl)oxy]carbonyl}phenyl)carbamoyl]-4-[4-(methylsulfonyl)-1-piperazinyl]-1-pyrrolidinecarboxylateYield 78.8%

Reagents, catalysts & solvents 1

HCID 1049
Pyridine
Solvent

Procedure

To a solution of the compound prepared in Example 4 (0.20 g, 0.40 mmol) and 2-methyl-2-propanyl 4-aminobenzoate (0.154 g, 0.80 mmol) in pyridine (50 mL) was added 1-ethyl-3-(3-dimethyllaminopropyl)carbodiimide hydrochloride (0.630 mg 3.2 mmol) at 0° C. The reaction was stirred at room temperature for 18 h. The mixture was concentrated under reduced pressure and the resulting residue diluted with dichloromethane (20 mL). This solution was washed with brine, dried and concentrated. Purification by flash chromatography (silica gel, 40 g, 20-80% ethyl acetate/hexanes) gave the title compound (0.185 g, 65%) as a white solid.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additionthe resulting residue diluted with dichloromethane (20 mL)
  3. washThis solution was washed with brine
  4. customdried
  5. concentrationconcentrated
  6. customPurification by flash chromatography (silica gel, 40 g, 20-80% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-cfd8b255b343423ebabc91563bc2287d
Source dataset
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09394250B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes