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N-methyl-2-pyrrolidone → n-[(2,2-Dichloro-1-methylcyclopropyl)carbonyl]-4-[[(2,4,6-trimethylphenyl)carbonyl]amino]-l-phenylalanine

HRID 393440
Notes
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Reaction equation

HRID 393440 reaction equation
CC1C=C(C)C=C(C)C=1S([NH:13][C:14]1[CH:25]=[CH:24][C:17]([CH2:18][C@@H:19]([C:21]([OH:23])=[O:22])[NH2:20])=[CH:16][CH:15]=1)(=O)=O.[Cl:26][C:27]1([Cl:34])[CH2:29][C:28]1([CH3:33])[C:30](O)=[O:31].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)[C:46]2[CH:47]=C[CH:49]=[CH:50][C:45]=2N=N1.[CH3:62]CN(C(C)C)C(C)C.CN1[CH2:76][CH2:75][CH2:74][C:73]1=[O:77]>>[Cl:26][C:27]1([Cl:34])[CH2:29][C:28]1([C:30]([NH:20][C@H:19]([C:21]([OH:23])=[O:22])[CH2:18][C:17]1[CH:16]=[CH:15][C:14]([NH:13][C:73]([C:74]2[C:50]([CH3:49])=[CH:45][C:46]([CH3:47])=[CH:76][C:75]=2[CH3:62])=[O:77])=[CH:25][CH:24]=1)=[O:31])[CH3:33]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 5

HCID 13387N-methyl-2-pyrrolidoneHCID 81531DiisopropylethylamineHCID 1026212,2-Dichloro-1-methylcyclopropanecarboxylic acidHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 544513294-[[(2,4,6-trimethylphenyl)sulfonyl]amino]-L-phenylalanine

Product 1

HCID 54131599
n-[(2,2-Dichloro-1-methylcyclopropyl)carbonyl]-4-[[(2,4,6-trimethylphenyl)carbonyl]amino]-l-phenylalanine

Procedure

4-[[(2,4,6-Trimethylphenyl)sulfonyl]amino]-L-phenylalanine on Wang resin (0.30 g, 0.23 mmol), 2,2-dichloro-1-methylcyclopropane carboxylic acid (0.19 g, 1.14 mmol), BOP ((0.50 g, 1.14 mmol) and DIPEA (0.26 mL, 1.5 mmol) in N-methylpyrrolidinone (3 mL) was agitated for 3 hr. The mixture was filtered and the resin was washed with dichloromethane and methanol and was air dried. Treatment with 90% TFA in dichloromethane for 3 min effected cleavage from the resin. The mixture was filtered, the filtrate was concentrated and lyophilized from water to give N-[(2,2-dichloro-1-methylcyclopropyl)carbonyl]-4-[[(2,4,6-trimethylphenyl)carbonyl]amino]-L-phenylalanine as a white solid.

Workup

  1. filtrationThe mixture was filtered
  2. washthe resin was washed with dichloromethane and methanol
  3. customdried
  4. filtrationThe mixture was filtered
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-ad849bd6f0684d38bb4a769cc773c319
Source dataset
uspto-grants-2004_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06806365B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes