Pyridine → 2-[(1-Tert-butoxycarbonylamino-cyclopentanecarbonyl)-amino]-3-(4-trifluoromethanesulfonyloxy-phenyl)-propionic acid ethyl ester

HRID 1166296Notes

Reaction equation

HRID 1166296 reaction equation
[F:1][C:2]([F:15])([F:14])[S:3]([O:6]S(C(F)(F)F)(=O)=O)(=[O:5])=[O:4].[CH2:16]([O:18][C:19](=[O:45])[CH:20]([NH:29][C:30]([C:32]1([NH:37][C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:36][CH2:35][CH2:34][CH2:33]1)=[O:31])[CH2:21][C:22]1[CH:27]=[CH:26][C:25](O)=[CH:24][CH:23]=1)[CH3:17].N1C=CC=CC=1>C(Cl)Cl>[CH2:16]([O:18][C:19](=[O:45])[CH:20]([NH:29][C:30]([C:32]1([NH:37][C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:36][CH2:35][CH2:34][CH2:33]1)=[O:31])[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([O:6][S:3]([C:2]([F:15])([F:14])[F:1])(=[O:5])=[O:4])=[CH:24][CH:23]=1)[CH3:17]

Participants

5

Reactant 3

HCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 700271362-[(1-Tert-butoxycarbonylamino-cyclopentanecarbonyl)-amino]-3-(4-hydroxy-phenyl)-propionic acid ethyl ester

Product 1

HCID 543615652-[(1-Tert-butoxycarbonylamino-cyclopentanecarbonyl)-amino]-3-(4-trifluoromethanesulfonyloxy-phenyl)-propionic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

1.2 mL of Trifluoromethanesulfonic anhydride (7.1 mmol) is added slowly dropwise to a solution of 2-[(1-tert-butoxycarbonylamino-cyclopentanecarbonyl)-amino]-3-(4-hydroxy-phenyl)-propionic acid ethyl ester (2.70 g, 6.4 mmol) and 0.7 mL (8.7 mmol) of pyridine in 20 mL of CH2Cl2 at 0° C., and the solution is stirred at 0° C. for 1 hour. The reaction mixture is then partitioned between water and CH2Cl2. The organic phase is separated and washed with saturated aqueous NaHCO3 solution, dried over MgSO4, filtered, and concentrated to yield 2-[(1-tert-butoxycarbonylamino-cyclopentanecarbonyl)-amino]-3-(4-trifluoromethanesulfonyloxy-phenyl)-propionic acid ethyl ester as a tan solid; 1H NMR (250 MHz, CDCl3) δ 7.25 (d, 2H), 7.17 (d, 2H), 4.80 (q, 1H), 4.75 (s, 1H), 4.10 (two quartets, 2H), 3.12 (ABX m, 2H), 2.00-2.20 (m, 2H), 1.60-2.00 (m, 6H), 1.40 (s, 9H), 1.18 (t, 3H).

Workup

  1. customThe reaction mixture is then partitioned between water and CH2Cl2
  2. customThe organic phase is separated
  3. washwashed with saturated aqueous NaHCO3 solution
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6ce1ceae313d4c7595195d380c27012b
Source dataset
uspto-grants-2003_09
Patent number
US06613782B2

Reaction notes

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