4-Methylmorpholine → 4-(Pyridin-4-yl)butanoyl-sarcosine ethyl ester

HRID 618148Notes

Reaction equation

HRID 618148 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][CH2:9][C:10]([OH:12])=O)=[CH:3][CH:2]=1.[NH:13]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH3:14].Cl.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.CN1CCOCC1>CN(C=O)C.CCOC(C)=O>[CH2:19]([O:18][C:16](=[O:17])[CH2:15][N:13]([C:10](=[O:12])[CH2:9][CH2:8][CH2:7][C:4]1[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=1)[CH3:14])[CH3:20]

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 171173Ethyl N-methylaminoacetate hydrochlorideHCID 31596254-Pyridinebutanoic acid

Product 1

HCID 216997624-(Pyridin-4-yl)butanoyl-sarcosine ethyl ester

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-(4-Pyridyl)butanoic acid 10-5 (100 mg, 1.8 mmol), H-Sar-OEt·HCl (300 mg, 2.0 mmol), BOP (965 mg, 2.2 mmol) and NMM (700 μL, 6.4 mmol) were combined in 9 mL DMF. After stirring overnight the mixture was diluted with EtOAc, washed with water (4×), sat. NaHCO3, and brine, dried (MgSO4), filtered and concentrated. Flash chromatography (silica, 80% to 100% EtOAc/hexane) provided 6-1 as a colorless oil.

Workup

  1. washwashed with water (4×), sat. NaHCO3, and brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-54f1554e798b416497e1eb0a6c6b3664
Source dataset
uspto-grants-1999_09
Patent number
US05952306

Reaction notes

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