Triethylamine → HCID 57518605, compound

HRID 1258117Notes

Reaction equation

HRID 1258117 reaction equation
[OH:1][CH2:2][C@H:3]1[CH2:7][CH2:6][C@:5]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:8])[C:4]1([CH3:18])[CH3:17].C(N(CC)CC)C.[CH3:26][S:27](Cl)(=[O:29])=[O:28]>ClCCl.O>[C:12]([O:11][C:10]([NH:9][C@:5]1([CH3:8])[CH2:6][CH2:7][C@H:3]([CH2:2][O:1][S:27]([CH3:26])(=[O:29])=[O:28])[C:4]1([CH3:18])[CH3:17])=[O:16])([CH3:15])([CH3:14])[CH3:13]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 46853229HCID 46853229, compound

Product 1

HCID 57518605HCID 57518605, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of t-butyl [(1R,3S)-3-(hydroxymethyl)-1,2,2-trimethyl cyclopentyl]carbamate (2.0 g, 7.78 mmol) in 30 mL of dichloromethane maintained at 0° C., triethylamine (5.4 mL, 38.9 mmol) was added. To this reaction mixture, methanesulphonyl chloride (1.91 mL, 23.3 mmol) was added dropwise over a period of 30 minutes and the stirring continued for two hours. Subsequently, the reaction mixture was diluted with dichloromethane and water. The layers were separated and the organic layer was dried over anhydrous Na2SO4, concentrated and dried to give a light yellow colored crude sticky mass, which was purified by column chromatography to furnish methanesulfonic acid (1S,3R)-3-t-butoxycarbonylamino-2,2,3-trimethyl-cyclopentylmethyl ester (2.01 g) in 76% yield as an off-white solid. 1H NMR (400 MHz, CDCl3) δ ppm 0.85 (s, 3H), 1.05 (s, 3H), 1.32 (s, 3H), 1.43 (s, 9H), 1.49 (m, 1H), 1.85-2.04 (m, 3H), 2.20-2.24 (m, 1H), 3.01 (s, 3H), 4.10-4.15 (dd, J=8 & 9.24 Hz, 1H), 4.24-4.29 (dd, J=6.44 & 9.52 Hz, 1H), 4.47 (s, 1H); m/z (M−55): 280.1; [α]D +36.3° (C., 1.0, methanol).

Workup

  1. customThe layers were separated
  2. dry with materialthe organic layer was dried over anhydrous Na2SO4
  3. concentrationconcentrated
  4. customdried
  5. customto give a light yellow colored crude sticky mass, which
  6. customwas purified by column chromatography

Sources & evidence

ORD record
ord-f6c42fce6adb46f88b5dd61fa59af863
Source dataset
uspto-grants-2013_06
Patent number
US08466145B2

Reaction notes

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