Diethylamine → HCID 86718858, compound

HRID 625143Notes

Reaction equation

HRID 625143 reaction equation
C1C2C(COC(=O)[NH:17][C@H:18]([CH2:27][C:28](=[O:68])[NH:29][C@H:30]([C:57](=[O:67])[NH:58][C:59]3[CH:64]=[CH:63][C:62]([CH2:65][OH:66])=[CH:61][CH:60]=3)[CH2:31][CH2:32][CH2:33][CH2:34][NH:35][C:36]([C:49]3[CH:54]=[CH:53][C:52]([O:55][CH3:56])=[CH:51][CH:50]=3)([C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[CH2:19][C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)C3C(=CC=CC=3)C=2C=CC=1.C(NCC)C>C1COCC1>[OH:66][CH2:65][C:62]1[CH:63]=[CH:64][C:59]([NH:58][C:57](=[O:67])[C@@H:30]([NH:29][C:28](=[O:68])[CH2:27][C@@H:18]([NH2:17])[CH2:19][C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)[CH2:31][CH2:32][CH2:33][CH2:34][NH:35][C:36]([C:49]2[CH:50]=[CH:51][C:52]([O:55][CH3:56])=[CH:53][CH:54]=2)([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)=[CH:60][CH:61]=1

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 86718859HCID 86718859, compound

Product 1

HCID 86718858HCID 86718858, compoundYield 0%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a 50 mL round-bottomed flask, the above prepared {(S)-2-(4-fluoro-phenyl)-1-[((S)-1-(4-hydroxymethyl-phenylcarbamoyl)-5-{[(4-methoxy-phenyl)-diphenyl-methyl]-amino}-pentylcarbamoyl)-methyl]-ethyl}-carbamic acid 9H-fluoren-9-ylmethyl ester (793 mg, 857 mol, Eq: 1.001) was combined with THF (12 ml) to give a brownish solution. At 0°, diethylamine (1.13 g, 1.59 ml, 15.4 mmol, Eq: 18) was added. The reaction was stirred at ambient temperature over night. The mixture was poured onto crashed ice/NH4Cl (pH ˜7), extracted 2× with AcOEt, washed with H2O and brine, dried over Na2SO4, and evaporated to dryness. Flash chromatography SiO2/10% MeOH/0.1% NEt3 in CH2Cl2 yielded 500 mg of the title compound as off-white solid. MS: expected mass: 702.3581, found mass: 702.3578.

Workup

  1. customto give a brownish solution
  2. additionThe mixture was poured
  3. extractionextracted 2× with AcOEt
  4. washwashed with H2O and brine
  5. dry with materialdried over Na2SO4
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-25b110cbbc8149cdb7f995a77a778eb8
Source dataset
uspto-grants-2016_04
Patent number
US09301990B2

Reaction notes

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