Diisopropylethylamine → HCID 86633223, compound

HRID 658141Notes

Reaction equation

HRID 658141 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([NH:12][C@H:13]([C:20]([O-:22])=[O:21])[C@H:14]([OH:19])[C:15]([O:17][CH3:18])=[O:16])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:23]CN(C(C)C)C(C)C>CN(C=O)C>[C:1]([O:5][C:6]([NH:8][C@@H:9]([C:10]([NH:12][C@H:13]([C:20]([OH:22])=[O:21])[C@H:14]([OH:19])[C:15]([O:17][CH3:18])=[O:16])=[O:11])[CH3:23])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 81531DiisopropylethylamineHCID 86633224HCID 86633224, compound

Product 1

HCID 86633223HCID 86633223, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The compound of example 255A (470 mg, 1.32 mmol) and (2S,3S)-2-amino-3-hydroxy-4-methoxy-4-oxobutyric acid hydrochloride (see example 33A for preparation, 407 mg, 2.04 mmol, 1.6 equivalents) are dissolved in DMF (20 ml) at 0° C., and DIPEA (1.78 ml, 10.20 mmol, 7.7 equivalents) are added. The mixture is stirred at room temperature for about 16 h and then chromatographed according to method 45 and fine purified by method 32. Yield: 200 mg (29% of theory).

Workup

  1. customchromatographed
  2. customfine purified by method 32

Sources & evidence

ORD record
ord-8cdf8e8723c74ee89694e3aff975c97c
Source dataset
uspto-grants-2011_12
Patent number
US08076285B2

Reaction notes

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