Water → HCID 178453662, compound

HRID 1159363Notes

Reaction equation

HRID 1159363 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 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Inter-mediate 10, tert-butyl [(cis-3-hydroxycyclobutyl)methyl]carbamate (3 g, 15 mmol) and triethylamine (5.2 mL, 36 mmol) were dissolved in CH2Cl2 (50 mL). MsCl (1.4 mL, 18 mmol) was added dropwise under stirring and cooling with an ice bath in argon. The temperature was brought to ambient within 1 h. Water (50 mL) was added, and the layers were separated. The organic one was washed with water, brine, dried with Na2SO4, and evaporated. The title compound (3.5 g, 85%) was obtained as a yellow oil. 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. temperaturecooling with an ice bath in argon
  2. customthe layers were separated
  3. washThe organic one was washed with water, brine
  4. dry with materialdried with Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-b21f814cffd24f33ba1404544d4be7b0
Source dataset
uspto-grants-2010_10
Patent number
US07812040B2

Reaction notes

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