1-Hydroxybenzotriazole → tert-Butyl 6-benzyloxy-3-(methoxymethylcarbamoyl)hexanoate

HRID 1912073Notes

Reaction equation

HRID 1912073 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH:12]([CH2:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C:13]([O-:15])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.CN[O:27][CH3:28].C1C=CC2N(O)N=[N:35][C:33]=2C=1.CCN=C=NCCCN(C)C.Cl>O.CN(C=O)C.C(N(CC)CC)C>[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH:12]([C:13](=[O:15])[NH:35][CH2:33][O:27][CH3:28])[CH2:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 866750434-tert-Butyl 2-(3-benzyloxypropyl)succinate

Product 1

HCID 71114707tert-Butyl 6-benzyloxy-3-(methoxymethylcarbamoyl)hexanoate

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

4-tert-Butyl 2-(3-benzyloxypropyl)succinate (80 g), triethylamine (48.4 mL) and DMF (400 mL) were mixed. To the mixture were added N,O-dimethylhydroxylamine hydrochloride (31.5 g), HOBt.H2O (45.6 g) and WSC.HCl (57.1 g) at ice temperature. The mixture was stirred at RT overnight. To the reaction mixture was added water (400 mL), and the mixture was extracted with hexane (480 mL, 480 mL, 240 mL). The combined organic layer was washed with aqueous 10 w/v % sodium carbonate (240 mL×3), aqueous 10 w/v % potassium hydrogen sulfate (240 mL), water (240 mL) and brine (240 mL), then dried over magnesium sulfate. The magnesium sulfate was filtered off and the filtrate was concentrated in vacuo to give the title compound (84.1 g) as a crude product.

Workup

  1. extractionthe mixture was extracted with hexane (480 mL, 480 mL, 240 mL)
  2. washThe combined organic layer was washed with aqueous 10 w/v % sodium carbonate (240 mL×3), aqueous 10 w/v % potassium hydrogen sulfate (240 mL), water (240 mL) and brine (240 mL)
  3. dry with materialdried over magnesium sulfate
  4. filtrationThe magnesium sulfate was filtered off
  5. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-02b0ae7dd9114c44b291f09a85f9c779
Source dataset
uspto-grants-2013_12
Patent number
US08604069B2

Reaction notes

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