Water → HCID 178453662, compound

HRID 1159391Notes

Reaction equation

HRID 1159391 reaction equation
[OH:1][C@@H:2]1[CH2:5][C@H:4]([CH2:6][NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:3]1.C(N(CC)CC)C.[CH3:22][S:23](Cl)(=[O:25])=[O:24].O>C(Cl)Cl>[CH3:22][S:23]([O:1][C@H:2]1[CH2:5][C@@H:4]([CH2:6][NH:7][C:8]([O:9][C:10]([CH3:11])([CH3:13])[CH3:12])=[O:14])[CH2:3]1)(=[O:25])=[O:24]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 178453655HCID 178453655, compound

Product 1

HCID 178453662HCID 178453662, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Intermediate 29, tert-Butyl [(cis-3-Hydroxycyclobutyl)methyl]carbamate (5.15 g, 26 mmol) and triethylamine (8.9 mL, 61 mmol) were dissolved in CH2Cl2 (50 mL). MsCl (2.4 mL, 31 mmol) was added dropwise at −20° C. under stirring in argon. The temperature was brought to ambient within 1 h. Water (100 mL) was added, and the layers were separated. The organic one was washed with water, brine, dried with Na2SO4, and evaporated, to give the title compound (5 g, 70%) white crystals. This crude product was used for the next stage without additional purification. 1H NMR-data (DMSO-d6): 6.74-7.00 (m, 1H, NH); 4.73-4.86 (m, 1H); 3.10 (s, 3H, MS); 2.97 (t, 2H, CH2, J=5.7 Hz); 2.32-2.42 (m, 2H); 1.80-2.43 (m, 3H); 1.38 (s, 9H, Boc).

Workup

  1. customthe layers were separated
  2. washThe organic one was washed with water, brine
  3. dry with materialdried with Na2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-807cd78fdc2d4474b3d61f6ed8dea735
Source dataset
uspto-grants-2010_10
Patent number
US07812040B2

Reaction notes

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