4-Methylmorpholine → HCID 57166654, compound

HRID 1647274Notes

Reaction equation

HRID 1647274 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:13]([OH:15])=O)[CH:10]([CH3:12])[CH3:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C=CC2N(O)N=NC=2C=1.C1CCC(N=C=NC2CCCCC2)CC1.Cl.Cl.[NH2:43][C@@H:44]([CH2:57][C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1)[C@@H:45]([OH:56])[CH2:46][N:47]1[CH2:51][CH2:50][CH2:49][C@H:48]1[C:52]([F:55])([F:54])[F:53].CN1CCOCC1>ClCCl>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:13]([NH:43][C@@H:44]([CH2:57][C:58]1[CH:59]=[CH:60][CH:61]=[CH:62][CH:63]=1)[C@@H:45]([OH:56])[CH2:46][N:47]1[CH2:51][CH2:50][CH2:49][C@H:48]1[C:52]([F:55])([F:53])[F:54])=[O:15])[CH:10]([CH3:11])[CH3:12])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 83693Boc-L-ValineHCID 86748768HCID 86748768, compound

Product 1

HCID 57166654HCID 57166654, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A stirred solution, cooled to 0° C., of 4.81 g (22.13 mmol) of N-(tert-butoxycarbonyl)-L-valine and 3.29 g (24.35 mmol) of HOBT in 40 ml of anhydrous dichloromethane was treated with 5.29 g (25.65 mmol) of DCC and stirred for 5 min. A solution of 3.70 g (20.12 mmol) of the compound from Example 2 and 8.85 ml (80.48 mmol) of N-methylmorpholine in 30 l of dichloromethane was then added dropwise. The cooling bath was removed and the reaction solution was stirred at room temperature for 2 h. The end of the reaction was determined by thin layer chromatography. The resulting urea was removed by filtration, the filtrate was concentrated in vacuo, and the crude product was purified by chromatography on 400 g of silica gel (dichloromethane: methanol). 6.89 g (68% of theory) of the title compound were obtained as a colourless foam. Rf = MS (DCI, NH3): m/e=503 (M+H)+

Workup

  1. customThe cooling bath was removed
  2. stirringthe reaction solution was stirred at room temperature for 2 h
  3. customThe resulting urea was removed by filtration
  4. concentrationthe filtrate was concentrated in vacuo
  5. customthe crude product was purified by chromatography on 400 g of silica gel (dichloromethane: methanol)

Sources & evidence

ORD record
ord-ea855b0a52ce4868beef3106ca2ce6e1
Source dataset
uspto-grants-1995_07
Patent number
US05430151

Reaction notes

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