4-Methylmorpholine → N-[(benzyloxy)carbonyl]-3-[(1-propylbutyl)sulfonyl)alanine

HRID 857266Notes

Reaction equation

HRID 857266 reaction equation
[CH2:1]([CH:4]([S:8]([CH2:11][C@@H:12]([C:14]([OH:16])=[O:15])[NH2:13])(=[O:10])=[O:9])[CH2:5][CH2:6][CH3:7])[CH2:2][CH3:3].[C:17](NC(=O)CCC(N)=O)([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18].CN1CCOCC1>C(Cl)Cl>[CH2:20]([O:19][C:17]([NH:13][C@H:12]([C:14]([OH:16])=[O:15])[CH2:11][S:8]([CH:4]([CH2:5][CH2:6][CH3:7])[CH2:1][CH2:2][CH3:3])(=[O:9])=[O:10])=[O:18])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 54145340N-CBZ succinamideHCID 574872803-[(1-Propylbutyl)sulfonyl]alanine

Product 1

HCID 57508140N-[(benzyloxy)carbonyl]-3-[(1-propylbutyl)sulfonyl)alanine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-[(1-Propylbutyl)sulfonyl]alanine (LXXXIII, 7.8 g, 27 mmole) and N-CBZ succinamide (7.4 g, 30 mmole) are mixed in methylene chloride (100 ml). The reaction is cooled to 0°, and NMM (6.9 g) is added dropwise. The reaction is allowed to warm to 20–25° and stirred for 4 hours at which point HPLC analysis indicated complete reaction. The reaction mixtue is concentrated under reduced pressure and partitioned between ethyl acetate and hydrochloric acid (1 N). The organic phase is washed with water, saline, dried over sodium sulfate, and concentrated under reduced pressure to give N-[(benzyloxy)carbonyl]-3-[(1-propylbutyl)sulfonyl]alanine (LXXXIV) that is used without further purification, M+H=386.

Workup

  1. temperatureThe reaction is cooled to 0°
  2. temperatureto warm to 20–25°
  3. customreaction
  4. concentrationThe reaction mixtue is concentrated under reduced pressure
  5. custompartitioned between ethyl acetate and hydrochloric acid (1 N)
  6. washThe organic phase is washed with water, saline
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5d72d26b5cc54ad386dcd8f108e15705
Source dataset
uspto-grants-2006_12
Patent number
US07144897B2

Reaction notes

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