Trifluoroacetic acid → HCID 88115281, compound

HRID 1369265Notes

Reaction equation

HRID 1369265 reaction equation
[CH2:1]([O:3][P:4]([CH:9]([C:18]1[CH:23]=[CH:22][C:21]([CH2:24][C@H:25]([NH:48]C(OC(C)(C)C)=O)[C:26](=[O:47])[NH:27][C@H:28]([C:30]2[CH:35]=[CH:34][C:33]([O:36][CH2:37][CH:38]3[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]3)=[C:32]([C:44](=[O:46])[NH2:45])[CH:31]=2)[CH3:29])=[CH:20][CH:19]=1)[P:10]([O:15][CH2:16][CH3:17])([O:12][CH2:13][CH3:14])=[O:11])(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:13]([O:12][P:10]([CH:9]([C:18]1[CH:19]=[CH:20][C:21]([CH2:24][C@H:25]([NH2:48])[C:26](=[O:47])[NH:27][C@H:28]([C:30]2[CH:35]=[CH:34][C:33]([O:36][CH2:37][CH:38]3[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43]3)=[C:32]([C:44](=[O:46])[NH2:45])[CH:31]=2)[CH3:29])=[CH:22][CH:23]=1)[P:4]([O:5][CH2:6][CH3:7])([O:3][CH2:1][CH3:2])=[O:8])(=[O:11])[O:15][CH2:16][CH3:17])[CH3:14]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 10843084HCID 10843084, compound

Product 1

HCID 88115281HCID 88115281, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To [(4-{(S)-2-tert-Butoxycarbonylamino-2-[(S)-1-(3-carbamoyl-4-cyclohexylmethoxy-phenyl)-ethylcarbamoyl]-ethyl}-phenyl)-(diethoxy-phosphoryl)-methyl]-phosphonic acid diethyl ester (2.8 g, 3.5 mmol) in methylene chloride (20 mL) was added TFA (6 mL). The mixture was stirred for 20 min., evaporated to dryness, and dissolved in DMSO (30 mL). Purification by RP HPLC (CH3CN/H2O) and lyophylization yielded a white solid (1.9 g, 2.3 mmol, 66%). MS [M+H]+ 710.

Workup

  1. customevaporated to dryness
  2. dissolutiondissolved in DMSO (30 mL)
  3. customPurification by RP HPLC (CH3CN/H2O) and lyophylization

Sources & evidence

ORD record
ord-ccb709dadf824e9e988309222826c198
Source dataset
uspto-grants-2003_06
Patent number
US06576766B1

Reaction notes

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