1-Hydroxybenzotriazole → tert-Butyl 5-(tert-butyldiphenylsilanyloxy)-3-methoxymethylcarbamoylvalerate

HRID 1912050Notes

Reaction equation

HRID 1912050 reaction equation
[Si:1]([O:18][CH2:19][CH2:20][CH:21]([CH2:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[C:22]([O-:24])=O)([C:14]([CH3:17])([CH3:16])[CH3:15])([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.Cl.CN[O:36][CH3:37].C1C=CC2N(O)N=[N:44][C:42]=2C=1.CCN=C=NCCCN(C)C.Cl>O.CN(C=O)C.C(N(CC)CC)C>[Si:1]([O:18][CH2:19][CH2:20][CH:21]([C:22](=[O:24])[NH:44][CH2:42][O:36][CH3:37])[CH2:25][C:26]([O:28][C:29]([CH3:31])([CH3:32])[CH3:30])=[O:27])([C:14]([CH3:17])([CH3:15])[CH3:16])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[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 866750344-tert-Butyl 2-[2-(tert-butyldiphenylsilanyloxy)ethyl]succinate

Product 1

HCID 71114767tert-Butyl 5-(tert-butyldiphenylsilanyloxy)-3-methoxymethylcarbamoylvalerate

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

4-tert-Butyl 2-[2-(tert-butyldiphenylsilanyloxy)ethyl]succinate (437.4 g), triethylamine (171 mL) and DMF (2000 mL) were mixed. To the mixture were added N,O-dimethylhydroxylamine hydrochloride (111 g), HOBt.H2O (161 g) and WSC.HCl (201 g) at ice temperature. After stirring at RT overnight, water (800 mL) was poured into the reaction mixture and the mixture was extracted with hexane (2.4 L). The organic layer was washed with water (1.2 L) and 10 w/v % saline solution (1.2 L). The aqueous layer was extracted with hexane (2.4 L) once again and the combined organic layer was dried over sodium sulfate. The sodium sulfate was filtered off and the filtrate was concentrated in vacuo to give the title compound (425.1 g) as a crude product.

Workup

  1. extractionthe mixture was extracted with hexane (2.4 L)
  2. washThe organic layer was washed with water (1.2 L) and 10 w/v % saline solution (1.2 L)
  3. extractionThe aqueous layer was extracted with hexane (2.4 L) once again
  4. dry with materialthe combined organic layer was dried over sodium sulfate
  5. filtrationThe sodium sulfate was filtered off
  6. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-c72f7167c5c946c089c4f0c40f8ff930
Source dataset
uspto-grants-2013_12
Patent number
US08604069B2

Reaction notes

Loading…