Dichloromethane → HCID 59828819, compound

HRID 1191023Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:11]=[N:12][C:13]([CH2:16]O)=[CH:14][CH:15]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.C(Cl)[Cl:26].CS(Cl)(=O)=O>O.C([O-])(O)=O.[Na+]>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:11]=[N:12][C:13]([CH2:16][Cl:26])=[CH:14][CH:15]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

Add 3-(tert-butoxycarbonylamino-methyl)-6-hydroxymethyl-pyridine (2.3 g, 9.65 mmol) and triethylamine (2.05 mL, 14.5 mmol) to DCM (30 mL). Cool the mixture to 0° C. and add methanesulfonyl chloride (0.83 mL, 10.6 mmol) to the mixture. Allow the mixture to warm to room temperature and stir overnight. Dilute the mixture with water (10 mL) and saturated aqueous NaHCO3 (10 mL). Separate the layers, and extract the aqueous layer with DCM (3×20 mL). Dry the combined organic extracts over Na2SO4, filter and concentrate in vacuo. Purify by chromatography on silica gel (80 g) eluting with hexane/EtOAc (1:0 to 1:1 gradient over 60 min, 80 mL/min) to obtain the desired intermediate as a colorless oil (1.14 g, 46%). MS (APCI+) m/z: 257 (M+H)+.

Workup

temperatureAllow the mixture to warm to room temperature
customSeparate the layers
extractionextract the aqueous layer with DCM (3×20 mL)
dry with materialDry the combined organic extracts over Na2SO4
filtrationfilter
concentrationconcentrate in vacuo
customPurify by chromatography on silica gel (80 g)
washeluting with hexane/EtOAc (1:0 to 1:1 gradient over 60 min, 80 mL/min)

Sources & evidence

ORD record: ord-9e771fdefc724a85a54d3cb406ff75e7
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08680091B2

Reaction notes

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