Diethyl Ether → HCID 15385696, compound

HRID 278634Notes

Reaction equation

HRID 278634 reaction equation
C([O:5][C:6](=[O:49])[C@H:7]([CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[NH:8][C:9]([O:11][CH2:12][CH:13]1[C:25]2[C:20](=[C:21]3[CH:33]=[CH:32][CH:31]=[CH:30][C:22]3=[C:23]3[CH:29]=[CH:28][CH:27]=[CH:26][C:24]3=2)[C:19]2[C:14]1=[C:15]1[CH:41]=[CH:40][CH:39]=[CH:38][C:16]1=[C:17]1[CH:37]=[CH:36][CH:35]=[CH:34][C:18]1=2)=[O:10])(C)(C)C.C(OCC)C>FC(F)(F)C(O)=O.O>[CH:41]1[C:15]2[C:16](=[C:17]3[CH:37]=[CH:36][CH:35]=[CH:34][C:18]3=[C:19]3[C:14]=2[CH:13]([CH2:12][O:11][C:9]([NH:8][C@H:7]([C:6]([OH:49])=[O:5])[CH2:42][C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)=[O:10])[C:25]2[C:20]3=[C:21]3[CH:33]=[CH:32][CH:31]=[CH:30][C:22]3=[C:23]3[CH:29]=[CH:28][CH:27]=[CH:26][C:24]3=2)[CH:38]=[CH:39][CH:40]=1

Participants

5

Reactant 2

HCID 3283Diethyl EtherHCID 57062129HCID 57062129, compound

Product 1

HCID 15385696HCID 15385696, compoundYield 92.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of Nα-17-tetrabenzo(a,c,g,i)fluorenylmethoxycarbonyl-L-phenylalanine tert-butyl ester (68.2 mg, 0.106 mmol) in trifluoroacetic acid (950 μl) and water (50 μl) was sonicated for 2.5 h. The solvent was removed in vacuo to give a purple residue. A mixture of diethyl ether and petrol b.p. 40-60° C. (1:1) was added. The precipitate obtained was chilled overnight, filtered, washed with petrol and finally dried in a vacuum desiccator over P2O5 to give compound (55) (57.6 mg, 93);

Workup

  1. customThe solvent was removed in vacuo
  2. customto give a purple residue
  3. additionwas added
  4. customThe precipitate obtained
  5. temperaturewas chilled overnight
  6. filtrationfiltered
  7. washwashed with petrol
  8. dry with materialfinally dried in a vacuum desiccator over P2O5

Sources & evidence

ORD record
ord-3d702b0fec21442cbe90f231c7209aea
Source dataset
uspto-grants-2002_03
Patent number
US06359113B1

Reaction notes

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