L-Leucine, N-((1,1-dimethylethoxy)carbonyl)- → [2-(6-Chloro-3,3-dimethoxy-hexahydrofuro[3,2-b]pyrrole-4-carbonyl)-3-methylbutyl]-carbamic acid tertbutyl ester

HRID 1258495Notes

Reaction equation

HRID 1258495 reaction equation
C(O[C:9]([N:11]1[CH2:15][CH:14]([Cl:16])[CH:13]2[O:17][CH2:18][C:19]([O:22][CH3:23])([O:20][CH3:21])[CH:12]12)=[O:10])C1C=CC=CC=1.[H][H].[C:26]([NH:33][C@H:34](C(O)=O)[CH2:35][CH:36]([CH3:38])[CH3:37])([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>[Pd]>[C:29]([O:28][C:26](=[O:27])[NH:33][CH2:34][CH:35]([C:9]([N:11]1[CH2:15][CH:14]([Cl:16])[CH:13]2[O:17][CH2:18][C:19]([O:20][CH3:21])([O:22][CH3:23])[CH:12]12)=[O:10])[CH:36]([CH3:37])[CH3:38])([CH3:32])([CH3:31])[CH3:30]

Participants

6

Reactant 4

HCID 83170L-Leucine, N-((1,1-dimethylethoxy)carbonyl)-HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 669298536-Chloro-3,3-dimethoxy-hexahydro-furo[3,2-b]pyrrole-4-carboxylic acid benzyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 86626338[2-(6-Chloro-3,3-dimethoxy-hexahydrofuro[3,2-b]pyrrole-4-carbonyl)-3-methylbutyl]-carbamic acid tertbutyl esterYield 93%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

6-Chloro-3,3-dimethoxy-hexahydro-furo[3,2-b]pyrrole-4-carboxylic acid benzyl ester (68 mg, 0.20 mmol) was deprotected by catalytic hydrogenation using 10% palladium on charcoal and hydrogen under atmospheric pressure. After stirring for 2 hours, the suspension was filtered through Celite and the filtrate evaporated on rotavapor to give the crude 6-chloro-3,3-dimethoxy-hexahydrofuro[3,2-b]pyrrole, which was coupled with N-Boc-leucine using HATU in the same way as the method described in Example 2, which gave the title compound (78 mg, 93%). MS m/z 421.2 (M+H)+.

Workup

  1. filtrationthe suspension was filtered through Celite
  2. customthe filtrate evaporated on rotavapor
  3. customto give the crude 6-chloro-3,3-dimethoxy-hexahydrofuro[3,2-b]pyrrole, which

Sources & evidence

ORD record
ord-9eb89ae18924445ba360214b3af4573c
Source dataset
uspto-grants-2013_06
Patent number
US08466158B2

Reaction notes

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