Dichloromethane → (S)-2-(3,5-Difluorophenyl)-1-((3S,9S,13S,15R,19S,22S)-15, 19-Dimethyl-2,8,12,18,21-pentaoxo-11-oxa-1,7,17,20-tetraaza-tetracyclo[20.4.0.03,7.013,17]hexacos-9-ylcarbamoyl)-ethylammonium 2,2,2-trifluoroacetate

HRID 751763Notes

Reaction equation

HRID 751763 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][C@H:10]([NH:47]C(=O)OC(C)(C)C)[C:11](=[O:46])[NH:12][C@H:13]2[CH2:38][O:37][C:36](=[O:39])[C@H:35]3[N:31]([CH2:32][C@H:33]([CH3:40])[CH2:34]3)[C:30](=[O:41])[C@H:29]([CH3:42])[NH:28][C:27](=[O:43])[C@H:26]3[N:21]([CH2:22][CH2:23][CH2:24][CH2:25]3)[C:20](=[O:44])[C@H:19]3[N:15]([CH2:16][CH2:17][CH2:18]3)[C:14]2=[O:45])[CH:5]=[C:6]([F:8])[CH:7]=1.ClCCl.[F:58][C:59]([F:64])([F:63])[C:60]([OH:62])=[O:61]>O>[F:58][C:59]([F:64])([F:63])[C:60]([O-:62])=[O:61].[F:8][C:6]1[CH:5]=[C:4]([CH2:9][C@H:10]([NH3+:47])[C:11](=[O:46])[NH:12][C@H:13]2[CH2:38][O:37][C:36](=[O:39])[C@H:35]3[N:31]([CH2:32][C@H:33]([CH3:40])[CH2:34]3)[C:30](=[O:41])[C@H:29]([CH3:42])[NH:28][C:27](=[O:43])[C@H:26]3[N:21]([CH2:22][CH2:23][CH2:24][CH2:25]3)[C:20](=[O:44])[C@H:19]3[N:15]([CH2:16][CH2:17][CH2:18]3)[C:14]2=[O:45])[CH:3]=[C:2]([F:1])[CH:7]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 59753410tert-Butyl [(S)-2-(3,5-difluorophenyl)-1-((3S,9S,13S,15R,19S,22S)-15,19-dimethyl-2,8,12,18,21-pentaoxo-11-oxa-1,7,17,20-tetraaza-tetracyclo-[20.4.0.03,7.013,17]hexacos-9-ylcarbamoyl)-ethyl]-carbamate

Product 1

HCID 86598033(S)-2-(3,5-Difluorophenyl)-1-((3S,9S,13S,15R,19S,22S)-15, 19-Dimethyl-2,8,12,18,21-pentaoxo-11-oxa-1,7,17,20-tetraaza-tetracyclo[20.4.0.03,7.013,17]hexacos-9-ylcarbamoyl)-ethylammonium 2,2,2-trifluoroacetate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

485 mg (0.64 mmol) of the compound from example 28A are introduced into dichloromethane (7 ml) at 0° C. 7 ml of a solution of 9 parts by volume of trifluoroacetic acid and 1 part of water are added and the reaction mixture is stirred for 45 min. The solvent is removed in vacuo and the residue is in each case taken up using dichloromethane and subsequently using toluene and concentrated to dryness. 588 mg of crude product are obtained, which is employed in the subsequent step without further purification.

Workup

  1. customThe solvent is removed in vacuo
  2. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-da3dda5360b84ac3ad9912c6c9dee906
Source dataset
uspto-grants-2008_07
Patent number
US07405201B2

Reaction notes

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