N-Methylbenzylamine → HCID 86585061, compound

HRID 1264408Notes

Reaction equation

HRID 1264408 reaction equation
[C:1]([C@H:4]1[N:8]([S:9]([C:12]2[CH:21]=[CH:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=2)(=[O:11])=[O:10])[CH2:7][C@H:6]([S:22][S:23][C@H:24]2[CH2:28][N:27]([S:29]([C:32]3[CH:41]=[CH:40][C:39]4[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=4)[CH:33]=3)(=[O:31])=[O:30])[C@H:26]([C:42](O)=[O:43])[CH2:25]2)[CH2:5]1)([OH:3])=O.C[N:46]1[CH2:51][CH2:50]OC[CH2:47]1.[B-](F)(F)(F)F.CN(C(ON1[C:70](=O)[CH:69]=[CH:68][CH:67]=[CH:66]1)=[N+](C)C)C.[CH3:72][NH:73][CH2:74][C:75]1[CH:80]=[CH:79][CH:78]=[CH:77][CH:76]=1.OS([O-])(=O)=O.[K+]>C(Cl)Cl>[CH2:51]([N:46]([CH3:47])[C:42]([C@@H:26]1[CH2:25][C@@H:24]([S:23][S:22][C@@H:6]2[CH2:5][C@@H:4]([C:1](=[O:3])[N:73]([CH2:74][C:75]3[CH:80]=[CH:79][CH:78]=[CH:77][CH:76]=3)[CH3:72])[N:8]([S:9]([C:12]3[CH:21]=[CH:20][C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[CH:13]=3)(=[O:10])=[O:11])[CH2:7]2)[CH2:28][N:27]1[S:29]([C:32]1[CH:41]=[CH:40][C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH:33]=1)(=[O:30])=[O:31])=[O:43])[C:50]1[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=1

Participants

7

Reactant 5

HCID 7669N-MethylbenzylamineHCID 79724-MethylmorpholineHCID 516920Potassium bisulfateHCID 2733204O-(2-Oxo-1(2H)-pyridyl)-N,N,N',N'-tetramethyluronium TetrafluoroborateHCID 11250934HCID 11250934, compound

Product 1

HCID 86585061HCID 86585061, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 300 mg (0.44 mmol) (2S,4R)-4-[(3R,5S)-5-Carboxy-1-(naphthalene-2-sulfonyl)-pyrrolidin-3-yldisulfanyl]-1-(naphthalene-2-sulfonyl)-pyrrolidine-2-carboxylic acid in 25 ml CH2Cl2 were added 100 μl (0.89 mmol, 1 eq) 4-methyl morpholine, followed by 331 mg (1.1 mmol, 1.25 eq) TPTU and 115 μl (0.89 mmol, 1 eq) N-methylbenzyl amine. The solution was stirred at RT over night. The mixture was added to a 1M KHSO4 solution, extracted with EtOAc and the organic phase was washed with 5% aq. NaHCO3 solution and brine. The solution was dried over Na2SO4, filtered and evaporated, yielding 313 mg (81%) (2S,4R)-4-[(3R,5S)-5-(Benzyl-methyl-carbamoyl)-1-(naphthalene-2-sulfonyl)-pyrrolidin-3-yldisulfanyl]-1-(naphthalene-2-sulfonyl)-pyrrolidine-2-carboxylic acid benzyl-methyl-amide as colorless foam, which was subjected to disulfide cleavage according to general procedure 4.1. to give (2S,4R)-4-Mercapto-1-(naphthalene-2-sulfonyl)-pyrrolidine-2-carboxylic acid benzyl-methyl-amide as white solid, MS: 441 (MH+).

Workup

  1. extractionextracted with EtOAc
  2. washthe organic phase was washed with 5% aq. NaHCO3 solution and brine
  3. dry with materialThe solution was dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-10ee81f29a5e49818587dfbeae156e71
Source dataset
uspto-grants-2003_04
Patent number
US06541638B2

Reaction notes

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