Hydrochloric Acid → HCID 66752380, compound

HRID 1815698Notes

Reaction equation

[C:1]([NH:5][C:6](=[O:8])[OH:7])([CH3:4])([CH3:3])[CH3:2].[CH:9]1([S:12]([NH2:15])(=[O:14])=[O:13])[CH2:11][CH2:10]1.[Li]CCCC.[CH3:21][O:22][CH2:23]Cl.Cl>C1COCC1>[C:1]([NH:5][C:6](=[O:7])[OH:8])([CH3:4])([CH3:3])[CH3:2].[CH3:21][O:22][CH2:23][NH:15][S:12]([CH:9]1[CH2:11][CH2:10]1)(=[O:14])=[O:13]

Participants

Conditions

Temperature: -78 °C

Procedure

Step 15IId) To a solution of cyclopropylsulfonylamine tert-butyl carbamate (1.0 g, 4.5 mmol) dissolved in THF (30 mL) cooled to −78° C., was added n-BuLi (6.4 mL, 10.2 mmol, 1.6 M in hexane) and the reaction mixture was stirred for 1 h. To this solution was added a neat solution of chloromethyl methyl ether (0.40 mL, 5.24 mmol), and the mixture was slowly allowed to warm to room temperature overnite. The solution pH was adjusted to 3 using 1N aqueous HCl and was then extracted with EtOAc (4×50 mL portions). The combined extracts were dried (MgSO4) and concentrated to afford Example 18, 1-methoxy-methylcyclopropylsulfonylamine tert-butylcarbamate, as a waxy solid (1.20 g, 100%) which was taken directly into the next reaction without further purification: 1H NMR (CDCl3) δ 1.03 (m, 2H), 1.52 (s, 9H), 1.66 (m, 2H), 3.38 (s, 3H), 3.68 (s, 2H), 7.54 (s, 1H); 13C NMR (CDCl3) δ 11.37, 28.29, 40.38, 58.94, 73.43, 83.61, 149.57.

Workup

temperatureto warm to room temperature overnite
extractionwas then extracted with EtOAc (4×50 mL portions)
dry with materialThe combined extracts were dried (MgSO4)
concentrationconcentrated

Sources & evidence

ORD record: ord-5da4398cdc03402f8e30c8e3932c98ba
Source dataset: uspto-grants-2005_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06878722B2

Reaction notes

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