Trifluoroacetic acid methylene chloride → (5R,9R)-9-dodecanamido-3,12-dioxo-1-phenyl-2-oxa-7-thia-4,11-diazatricosane-5-carboxylic acid

HRID 2407877Notes

Reaction equation

HRID 2407877 reaction equation
[C:1]([NH:14][C@H:15]([CH2:38][NH:39][C:40](=[O:52])[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH3:51])[CH2:16][S:17][CH2:18][C@@H:19]([C:31]([O:33]C(C)(C)C)=[O:32])[NH:20][C:21](=[O:30])[O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)(=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].C(O)(C(F)(F)F)=O.C(Cl)Cl>>[C:1]([NH:14][C@H:15]([CH2:38][NH:39][C:40](=[O:52])[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH3:51])[CH2:16][S:17][CH2:18][C@@H:19]([C:31]([OH:33])=[O:32])[NH:20][C:21](=[O:30])[O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)(=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 71294480(5R,9R)-tert-butyl 9-dodecanamido-3,12-dioxo-1-phenyl-2-oxa-7-thia-4,11-diazatricosane-5-carboxylate

Product 1

HCID 71294513(5R,9R)-9-dodecanamido-3,12-dioxo-1-phenyl-2-oxa-7-thia-4,11-diazatricosane-5-carboxylic acid

Procedure

(5R,9R)-tert-butyl 9-dodecanamido-3,12-dioxo-1-phenyl-2-oxa-7-thia-4,11-diazatricosane-5-carboxylate was stirred in a 30% TFA/DCM (0.05 M) solution for 2 hours at room temperature. The reaction was then concentrated and diluted with DCM. The organic phase was washed once with 1 M citric acid (pH3) then dried over anhydrous Na2SO4, filtered and concentrated to afford the title compound as a viscous oil that was used with no further purification.

Workup

  1. concentrationThe reaction was then concentrated
  2. additiondiluted with DCM
  3. washThe organic phase was washed once with 1 M citric acid (pH3)
  4. dry with materialthen dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ce501cd4b3a84ff2829776a46dd0a5f8
Source dataset
uspto-grants-2014_08
Patent number
US08808703B2

Reaction notes

Loading…