4-Methylmorpholine → HCID 86585062, compound

HRID 1264409Notes

Reaction equation

HRID 1264409 reaction equation
[C:1]([S:4][C@H:5]1[CH2:9][N:8]([S:10]([C:13]2[CH:22]=[CH:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:14]=2)(=[O:12])=[O:11])[C@H:7](C(O)=O)[CH2:6]1)(=[O:3])[CH3:2].CN1CC[O:30]CC1.[B-](F)(F)(F)F.CN(C(ON1C(=O)C=CC=C1)=[N+](C)C)C.[CH3:53][O:54][C:55](=[O:69])[C:56]1[CH:61]=[CH:60][C:59]([N:62]([CH3:68])[C:63](=[O:67])[CH2:64][NH:65][CH3:66])=[CH:58][CH:57]=1>C(Cl)Cl>[CH3:53][O:54][C:55](=[O:69])[C:56]1[CH:57]=[CH:58][C:59]([N:62]([C:63](=[O:67])[CH2:64][NH:65][C:66]([C@@H:7]2[CH2:6][C@@H:5]([S:4][C:1](=[O:3])[CH3:2])[CH2:9][N:8]2[S:10]([C:13]2[CH:22]=[CH:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:14]=2)(=[O:12])=[O:11])=[O:30])[CH3:68])=[CH:60][CH:61]=1

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 2733204O-(2-Oxo-1(2H)-pyridyl)-N,N,N',N'-tetramethyluronium TetrafluoroborateHCID 70001203HCID 70001203, compoundHCID 86585063HCID 86585063, compound

Product 1

HCID 86585062HCID 86585062, compoundYield 99.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(al) 150 mg (0.4 mmol) (2S,4R)-4-Acetylsulfanyl-1-(naphthalene-2-sulfonyl)-pyrrolidine-2-carboxylic acid in 10 ml CH2Cl2 were treated with 49 μl (0.43 mmol, 1.1 eq) 4-methyl morpholine, 142 mg (0.47 mmol, 1.2 eq) TPTU and 140 mg (0.59 mmol, 1.5 eq) 4-(methyl-methylaminoacetyl-amino)-benzoic acid methyl ester. The solution was stirred at RT over night. The mixture was concentrated and purified by flash chromatography yielding 233 mg (98%) (2S,4R)-4-[[[[4-Acetylsulfanyl-1-(naphthalene-2-sulfonyl)-pyrrolidine-2-carbonyl]-amino]-acetyl]-methyl-amino]-benzoic acid methyl ester as white foam, MS: 598 (MH+).

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by flash chromatography

Sources & evidence

ORD record
ord-1c456f25212a46528fddd8cfa8d2b045
Source dataset
uspto-grants-2003_04
Patent number
US06541638B2

Reaction notes

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