Water → HCID 69061123, compound

HRID 1432393Notes

Reaction equation

HRID 1432393 reaction equation
[C:1]([NH:20][C@H:21]([CH2:24][CH3:25])[CH:22]=[O:23])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:26][Li].O>CCOCC>[C:1]([NH:20][C@H:21]([CH2:24][CH3:25])[CH:22]([OH:23])[CH3:26])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 57714153(R)-2-(Trityl-amino)-butyraldehydeHCID 178418348HCID 178418348, compound

Product 1

HCID 69061123HCID 69061123, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a stirred solution of (R)-2-(trityl-amino)-butyraldehyde (0.59 g, 1.79 mmol) in Et2O (25 mL) under Ar at −70° C., was added methyl lithium (1.4 M in Et2O; 1.88 mL, 2.63 mmol) dropwise. The reaction mixture was stirred at this temperature for 30 min and then allowed to warm to RT over 15 min and stirred at this temperature for 1 h. The mixture was cooled to 0° C. to which was slowly added H2O (25 mL) and the solution was extracted between Et2O (100 mL) and H2O (100 mL). The aqueous phase was extracted with more Et2O (2×50 mL), and the combined organic phase was washed with brine (50 mL), dried (MgSO4) and evaporated in vacuo to afford the title compounds as a light yellow oil (0.58 g, 94%). 1H-NMR (d6-DMSO, 250 MHz): δ 0.42-0.57 (m, 3H, —NHCH(CH2CH3)CH(CH3)OH), 0.97-1.15 (m, 5H, —NHCH(CH2CH3)CH(CH3)OH+—NHCH(CH2CH3)CH(CH3)OH), 2.01 (m, 1H, —NHCH(CH2CH3)CH(CH3)OH), 3.26 (m, 1H, —NHCH(CH2CH3)CH(CH3)OH), 4.39 (d, 1H, J=4.10 Hz, —NHCH(CH2CH3)CH(CH3)OH), 7.13-7.50 (m, 15H, 3×Bz).

Workup

  1. stirringstirred at this temperature for 1 h
  2. temperatureThe mixture was cooled to 0° C. to which
  3. extractionthe solution was extracted between Et2O (100 mL) and H2O (100 mL)
  4. extractionThe aqueous phase was extracted with more Et2O (2×50 mL)
  5. washthe combined organic phase was washed with brine (50 mL)
  6. dry with materialdried (MgSO4)
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-f55da8d3ce36450699453f28d6dbf41e
Source dataset
uspto-grants-2009_11
Patent number
US07612079B2

Reaction notes

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