Di-tert-butyl (2S)-2-[(3-{[5-oxido-4-(phenylsulphonyl)-1,2,5-oxadiazol-3-yl]-oxy}-propionyl)-amino]-pentanedioate → (2S)-2-[(3-{[5-Oxido-4-(phenylsulphonyl)-1,2,5-oxadiazol-3-yl]-oxy}-propionyl)-amino]-pentanedioic Acid

HRID 1013435Notes

Reaction equation

HRID 1013435 reaction equation
[O-:1][N+:2]1[O:6][N:5]=[C:4]([O:7][CH2:8][CH2:9][C:10]([NH:12][C@@H:13]([CH2:21][CH2:22][C:23]([O:25]C(C)(C)C)=[O:24])[C:14]([O:16]C(C)(C)C)=[O:15])=[O:11])[C:3]=1[S:30]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)(=[O:32])=[O:31]>ClCCl.C(O)(C(F)(F)F)=O>[O-:1][N+:2]1[O:6][N:5]=[C:4]([O:7][CH2:8][CH2:9][C:10]([NH:12][C@@H:13]([CH2:21][CH2:22][C:23]([OH:25])=[O:24])[C:14]([OH:16])=[O:15])=[O:11])[C:3]=1[S:30]([C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)(=[O:31])=[O:32]

Participants

4

Reactant 1

HCID 67317279Di-tert-butyl (2S)-2-[(3-{[5-oxido-4-(phenylsulphonyl)-1,2,5-oxadiazol-3-yl]-oxy}-propionyl)-amino]-pentanedioate

Product 1

HCID 57626191(2S)-2-[(3-{[5-Oxido-4-(phenylsulphonyl)-1,2,5-oxadiazol-3-yl]-oxy}-propionyl)-amino]-pentanedioic Acid

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of the compound obtained in Step A (3 g-5.5 mmol) in 100 ml of dichloromethane and 15 ml of TFA is stirred for 6 hours under argon. The solvents are distilled off in vacuo. The residue is triturated in diisopropyl ether, filtered off with suction and then dried in vacuo to yield the expected product in the form of white crystals.

Workup

  1. distillationThe solvents are distilled off in vacuo
  2. customThe residue is triturated in diisopropyl ether
  3. filtrationfiltered off with suction
  4. customdried in vacuo

Sources & evidence

ORD record
ord-664d00725b2145178573f976119139a1
Source dataset
uspto-grants-2011_07
Patent number
US07981920B2

Reaction notes

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