Triethylamine → HCID 178484154, compound

HRID 1159368Notes

Reaction equation

HRID 1159368 reaction equation
C(NC[C@@H]1C[C@H](O)C1)C1C=CC=CC=1.[OH:15][C@@H:16]1[CH2:19][C@H:18]([CH2:20][N:21]([CH3:29])[C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:17]1.C(N(CC)CC)C.[CH3:37][S:38](Cl)(=[O:40])=[O:39]>C(Cl)Cl.O>[CH3:37][S:38]([O:15][C@H:16]1[CH2:19][C@@H:18]([CH2:20][N:21]([C:22]([O:23][C:24]([CH3:25])([CH3:26])[CH3:27])=[O:28])[CH3:29])[CH2:17]1)(=[O:40])=[O:39]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 178484138HCID 178484138, compoundHCID 178521632HCID 178521632, compound

Product 1

HCID 178484154HCID 178484154, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Intermediate 5, tert-Butyl [(cis-3-hydroxycyclobutyl)methyl]methylcarbamate (22.6 g, 105 mmol) and triethylamine (36 mL, 250 mmol) were dissolved in CH2Cl2 (50 mL). MsCl (9.75 mL, 126 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. The title compound (29 g, 96%) was obtained as a yellow oil. This crude product was used for the next stage without additional purification. 1H NMR-data (DMSO-d6): 4.76-4.88 (m, 1H); 3.23 (d, 2H, CH2, J=6.6 Hz); 3.12 (s, 3H, MS); 2.76 (s, 3H, NCH3); 2.38-2.48 (m, 2H); 2.00-2.12 (m, 1H); 1.86-97 (m, 2H); 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-86890f3f4eea48f09328e78b0776ba92
Source dataset
uspto-grants-2010_10
Patent number
US07812040B2

Reaction notes

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