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Benzyloxycarbonyl-L-methionine → 2-(morpholinomethyl)prop-2-yl (2S)-2-(benzyloxycarbonylamino)-4-methylsulfanylbutyrate

HRID 1251879
Notes
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Reaction equation

HRID 1251879 reaction equation
[OH:1][C:2]([CH3:11])([CH3:10])[CH2:3][N:4]1[CH2:9][CH2:8][O:7][CH2:6][CH2:5]1.[CH2:12]([O:19][C:20]([NH:22][C@H:23]([C:28](O)=[O:29])[CH2:24][CH2:25][S:26][CH3:27])=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.F[P-](F)(F)(F)(F)F.Br[P+](N1CCCC1)(N1CCCC1)N1CCCC1>CN(C1C=CN=CC=1)C.ClCCl>[CH2:12]([O:19][C:20]([NH:22][C@@H:23]([CH2:24][CH2:25][S:26][CH3:27])[C:28]([O:1][C:2]([CH2:3][N:4]1[CH2:5][CH2:6][O:7][CH2:8][CH2:9]1)([CH3:11])[CH3:10])=[O:29])=[O:21])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 1550857Benzyloxycarbonyl-L-methionineHCID 2733179PyBroPHCID 222731702-Methyl-1-morpholinopropan-2-ol

Product 1

HCID 865851352-(morpholinomethyl)prop-2-yl (2S)-2-(benzyloxycarbonylamino)-4-methylsulfanylbutyrateYield 40%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridine
Catalyst
HCID 6344DichloromethaneSolvent

Procedure

A solution of N-(2-hydroxy-2-methylpropyl)morpholine (9.8 g, 62 mmol), N-benzyloxycarbonyl-L-methionine (12.6 g, 44 mmol), bromo-tris-pyrrolidino-phosphonium hexafluorophosphate (25 g, 54 mmol), DMAP (5.4 g, 44 mmole) in dichloromethane (250 ml) was stirred, in the presence of 4 Å molecular sieves (5 g), at ambient temperature for 48 h. After evaporation to dryness, the mixture was taken up in diethyl ether and the insoluble material eliminated by filtration. The organic layer was washed with a saturated aqueous solution of sodium hydrogen carbonate and a saturated solution of brine, evaporated to dryness and purified by flash column chromatography eluting with dichloromethane/ethanol (98:2) to give 2-(morpholinomethyl)prop-2-yl (2S)-2-(benzyloxycarbonylamino)-4-methylsulfanylbutyrate (40%).

Workup

  1. customAfter evaporation to dryness
  2. filtrationthe insoluble material eliminated by filtration
  3. washThe organic layer was washed with a saturated aqueous solution of sodium hydrogen carbonate
  4. customa saturated solution of brine, evaporated to dryness
  5. custompurified by flash column chromatography
  6. washeluting with dichloromethane/ethanol (98:2)

Sources & evidence

ORD record
ord-fb2d2d95a9cc4d629489a2b647bfd7b1
Source dataset
uspto-grants-2002_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06342765B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes