4-Methylmorpholine → Boc-gly-pro-OH

HRID 483642

Reaction equation

HRID 483642 reaction equation
CN1CCOCC1.[NH:8]1[CH2:15][CH2:14][CH2:13][C@H:9]1[C:10]([OH:12])=[O:11].[NH:16]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:17][C:18](ON1C(=O)CCC1=O)=[O:19]>CN(C=O)C>[NH:16]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:17][C:18]([N:8]1[CH2:15][CH2:14][CH2:13][C@H:9]1[C:10]([OH:12])=[O:11])=[O:19]

Participants

5

Reactant 3

HCID 79724-Methylmorpholine2×HCID 76926N-(tert-Butyloxycarbonyl)glycine N-hydroxysuccinimide esterHCID 145742L-Proline

Product 1

HCID 11673468Boc-gly-pro-OH

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.4 ml (11 mmol) of N-methylmorpholine are added to 1.15 g (10 mmol) of proline in 50 ml of DMF. The mixture is cooled with an ice bath, 3.06 g (10 mmol) of Boc-Gly-OSu are then added and the pH is adjusted to between 6 and 7 throughout the reaction (14 h) by successive additions of small amounts of N-methylmorpholine (this substance is used as a proton acceptor). The DMF is evaporated off and the evaporation residue is taken up with AcOEt; after precipitation in petroleum ether and then filtration, the expected product is collected.

Workup

  1. temperatureThe mixture is cooled with an ice bath
  2. customThe DMF is evaporated off
  3. customafter precipitation in petroleum ether
  4. filtrationfiltration
  5. customthe expected product is collected

Sources & evidence

ORD record
ord-46a95c7b3d8442cca33271779bfafde1
Source dataset
uspto-grants-1993_07
Patent number
US05225532

Linked notes

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