Triethylamine → HCID 58868954, compound

HRID 1441971Notes

Reaction equation

HRID 1441971 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].[C:16]([O:20][C:21]([NH:23][C@H:24]([C:36]([O:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)=[O:37])[CH2:25][C:26]1[C:31]([N+:32]([O-:34])=[O:33])=[CH:30][CH:29]=[C:28](O)[CH:27]=1)=[O:22])([CH3:19])([CH3:18])[CH3:17].C(N(CC)CC)C.CC(C)=O.C(=O)=O>ClCCl.O>[C:16]([O:20][C:21]([NH:23][C@H:24]([C:36]([O:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)=[O:37])[CH2:25][C:26]1[CH:27]=[C:28]([O:6][S:3]([C:2]([F:15])([F:14])[F:1])(=[O:5])=[O:4])[CH:29]=[CH:30][C:31]=1[N+:32]([O-:34])=[O:33])=[O:22])([CH3:19])([CH3:17])[CH3:18]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 67749Trifluoromethanesulfonic anhydrideHCID 18522661Acetone cardiceHCID 58868931HCID 58868931, compound

Product 1

HCID 58868954HCID 58868954, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

1.0 ml (6.01 mmol) of trifluoromethanesulfonic anhydride is added dropwise to a solution of 2.27 g (5.46 mmol) of benzyl N-(tert-butoxycarbonyl)-3-hydroxy-6-nitro-L-phenylalaninate (Example 12I) and 1.52 ml (10.9 mmol) of triethylamine in 150 ml of dichloromethane at −15° C. (acetone/dry ice bath). After 15 min, the mixture is warmed to RT, and water is added. The organic phase is separated, washed several times with water, dried over magnesium sulfate and concentrated in vacuo. The crude product is purified by RP-HPLC (mobile phase: acetonitrile/water gradient).

Workup

  1. customThe organic phase is separated
  2. washwashed several times with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe crude product is purified by RP-HPLC (mobile phase: acetonitrile/water gradient)

Sources & evidence

ORD record
ord-e05686c2bd274fb4bc67cfc305157731
Source dataset
uspto-grants-2010_02
Patent number
US07655643B2

Reaction notes

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