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(5-Methyl-2-oxo-1,3-dioxol-4-yl)methyl 4-nitrophenyl carbonate → 2-[2-Chloro-1-(3,4,5-trihydroxy-6-methylsulfanyl-tetrahydro-pyran-2-yl)-propylcarbamoyl]-5-propyl-azepane-1-carboxylic acid 5-methyl-2-oxo-[1,3]dioxol-4-ylmethyl ester

HRID 854014
Notes
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Reaction equation

HRID 854014 reaction equation
[Cl:1][CH:2]([CH3:28])[CH:3]([NH:15][C:16]([CH:18]1[CH2:24][CH2:23][CH:22]([CH2:25][CH2:26][CH3:27])[CH2:21][CH2:20][NH:19]1)=[O:17])[CH:4]1[CH:9]([OH:10])[CH:8]([OH:11])[CH:7]([OH:12])[CH:6]([S:13][CH3:14])[O:5]1.[N+](C1C=CC([O:38][C:39](=O)[O:40][CH2:41][C:42]2[O:43][C:44](=[O:48])[O:45][C:46]=2[CH3:47])=CC=1)([O-])=O>CN(C=O)C>[CH3:47][C:46]1[O:45][C:44](=[O:48])[O:43][C:42]=1[CH2:41][O:40][C:39]([N:19]1[CH2:20][CH2:21][CH:22]([CH2:25][CH2:26][CH3:27])[CH2:23][CH2:24][CH:18]1[C:16](=[O:17])[NH:15][CH:3]([CH:4]1[CH:9]([OH:10])[CH:8]([OH:11])[CH:7]([OH:12])[CH:6]([S:13][CH3:14])[O:5]1)[CH:2]([Cl:1])[CH3:28])=[O:38]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 10756264(5-Methyl-2-oxo-1,3-dioxol-4-yl)methyl 4-nitrophenyl carbonateHCID 730964105-Propyl-azepane-2-carboxylic acid [2-chloro-1-(3,4,5-trihydroxy-6-methylsulfanyl-tetrahydro-pyran-2-yl)-propyl]-amide

Product 1

HCID 692210762-[2-Chloro-1-(3,4,5-trihydroxy-6-methylsulfanyl-tetrahydro-pyran-2-yl)-propylcarbamoyl]-5-propyl-azepane-1-carboxylic acid 5-methyl-2-oxo-[1,3]dioxol-4-ylmethyl esterYield 33.6%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

The title compound from example 47 (54 mg, 0.12 mmol) was dissolved in dry DMF (5 mL), then solid KHCO3 (25 mg, 0.25 mmol) and carbonic acid 5-methyl-2-oxo-[1,3]dioxol-4-ylmethyl ester 4-nitro-phenyl ester (40 mg, 0.14 mmol prepared as described in F. Sakamoto, et. al, Chem. Pharm. Bull. 1984, 32 (6), 2241-2348) were added. The resulting mixture was stirred for 16 h, and the solvents were removed under reduced pressure, then the residue was purified by chromatography on silica with 5% MeOH/DCM to provide the title compound (24 mg, 33%) as a white solid.

Workup

  1. customthe solvents were removed under reduced pressure
  2. customthe residue was purified by chromatography on silica with 5% MeOH/DCM

Sources & evidence

ORD record
ord-62062a83394c4962a4c4a881fa9e30a0
Source dataset
uspto-grants-2007_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07256177B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes