HCID 57027252, compound → HCID 54566941, compound

HRID 617710Notes

Reaction equation

HRID 617710 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:24]([O:26][C@H:27]([CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49])[CH2:28][C:29]([O:31]CC(Cl)(Cl)Cl)=[O:30])=[O:25])[CH2:13][CH2:14][CH2:15][NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)(=O)C.[Zn]>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:24]([O:26][C@H:27]([CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49])[CH2:28][C:29]([OH:31])=[O:30])=[O:25])[CH2:13][CH2:14][CH2:15][NH:16][C:17]([O:19][C:20]([CH3:21])([CH3:22])[CH3:23])=[O:18])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 57027252HCID 57027252, compound

Product 1

HCID 54566941HCID 54566941, compoundYield 104.8%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 2,2,2-trichloroethyl (3R)-3-[N2 -benzyloxycarbonyl-N5 -tert-butoxycarbonyl-L-ornithyl]oxy-hexadecanoate (100 mg) in 90% aqueous acetic acid (3 ml) was added zinc powder (400 mg) at 0° C. and stirred for 1 hour. After the reaction mixture was filtered, the filtrate was evaporated in vacuo. The residue was dissolved in ethyl acetate and washed with diluted hydrochloric acid. The organic layer was dried over with sodium sulfate and evaporated in vacuo to give (3R)-3-[N2 -benzyloxycarbonyl-N5 -tert-butoxycarbonyl-L-ornithyl]oxy-hexadecanoic acid (86.5 mg).

Workup

  1. filtrationAfter the reaction mixture was filtered
  2. customthe filtrate was evaporated in vacuo
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with diluted hydrochloric acid
  5. dry with materialThe organic layer was dried over with sodium sulfate
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-efc036f875014f87b826ee78d661ba7b
Source dataset
uspto-grants-1999_09
Patent number
US05952299

Reaction notes

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