Morpholine → benzyl(3S)-1-[(1S)-1-methyl-2-morpholin-4-yl-2-oxoethyl]-2-oxopyrrolidin-3-ylcarbamate

HRID 456495Notes

Reaction equation

HRID 456495 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[CH2:16][CH2:15][N:14]([C@@H:17]([CH3:21])[C:18]([OH:20])=O)[C:13]1=[O:22])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.[NH:54]1[CH2:59][CH2:58][O:57][CH2:56][CH2:55]1.[Cl-].[NH4+]>CN(C=O)C>[CH3:21][C@H:17]([N:14]1[CH2:15][CH2:16][C@H:12]([NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:13]1=[O:22])[C:18]([N:54]1[CH2:59][CH2:58][O:57][CH2:56][CH2:55]1)=[O:20]

Participants

7

Reactant 5

HCID 8083MorpholineHCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 16124766(2S)-2-((3S)-3-{[(Benzyloxy)carbonyl]amino}-2-oxopyrrolidin-1-yl)propanoic acid

Product 1

HCID 16125563benzyl(3S)-1-[(1S)-1-methyl-2-morpholin-4-yl-2-oxoethyl]-2-oxopyrrolidin-3-ylcarbamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(2S)-2-((3S)-3-{[(Benzyloxy)carbonyl]amino}-2-oxopyrrolidin-1-yl)propanoic acid (84.5 g) was dissolved in DMF (2 l) and O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (161 g) was added, followed by N,N-diisopropylethylamine (92 m)) and morpholine (46 ml). The mixture was stirred under nitrogen for 2.5 h, and saturated aqueous ammonium chloride was added. The mixture was stirred for 15 min then partitioned between water and ethyl acetate. The separated organic phase was washed with lithium chloride (10% by weight), followed by saturated sodium bicarbonate and brine. The organic layer was dried (over sodium sulphate) and concentrated under reduced pressure to give the title compound (65 g) as a yellow solid.

Workup

  1. stirringThe mixture was stirred for 15 min
  2. customthen partitioned between water and ethyl acetate
  3. washThe separated organic phase was washed with lithium chloride (10% by weight)
  4. dry with materialThe organic layer was dried (over sodium sulphate)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ab47e09daf844288a6d1cb6691047a98
Source dataset
uspto-grants-2007_03
Patent number
US07186717B2

Reaction notes

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