Methanol → HCID 69309649, compound

HRID 751475Notes

Reaction equation

HRID 751475 reaction equation
[C:1]([O:5][C:6](=[O:24])[NH:7][C@H:8]([C:13](=[O:23])[NH:14][CH:15]1[CH2:21][CH2:20][CH2:19][NH:18][CH2:17][CH:16]1[OH:22])[CH2:9][CH:10]([CH3:12])[CH3:11])([CH3:4])([CH3:3])[CH3:2].C(=O)(O)[O-].[Na+].[CH3:30][C:31]1[N:36]=[C:35]([S:37](Cl)(=[O:39])=[O:38])[CH:34]=[CH:33][CH:32]=1.CO>ClCCl.Cl>[C:1]([O:5][C:6](=[O:24])[NH:7][C@H:8]([C:13](=[O:23])[NH:14][CH:15]1[CH2:21][CH2:20][CH2:19][N:18]([S:37]([C:35]2[CH:34]=[CH:33][CH:32]=[C:31]([CH3:30])[N:36]=2)(=[O:39])=[O:38])[CH2:17][CH:16]1[OH:22])[CH2:9][CH:10]([CH3:12])[CH3:11])([CH3:3])([CH3:4])[CH3:2]

Participants

7

Reactant 4

HCID 887MethanolHCID 516892Sodium BicarbonateHCID 12076054HCID 12076054, compoundHCID 122954646-Methylpyridine-2-sulfonyl chloride

Product 1

HCID 69309649HCID 69309649, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of [(S)-1-(3-hydroxy-azepan-4-ylcarbamoyl)-3-methyl-butyl]-carbamic acid tert-butyl ester of Example 2 (1.0 g) in dichloromethane (20 mL) was added saturated sodium bicarbonate (50 mL). To this solution was added 6-methyl-pyridine-2-sulphonyl chloride (6.44 mL of a 0.13 g/mL solution in 9M HCl). The reaction was stirred until complete. Workup and column chromatography (5% methanol:dichloromethane) provided the title compound (1.2 g).

Sources & evidence

ORD record
ord-3daf72c3d2bd41b08d4d6127160c50e1
Source dataset
uspto-grants-2008_07
Patent number
US07405209B2

Reaction notes

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