Trifluoroacetic acid → HCID 44511932, compound

HRID 1022994Notes

Reaction equation

HRID 1022994 reaction equation
C(OC([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][C@H:13]([NH:21][C:22]([NH:24][C@@H:25]1[CH2:40][C:39]2=[CH:41][CH:42]=[C:36]([CH:37]=[CH:38]2)[O:35][CH2:34][CH2:33][CH2:32][CH2:31][O:30][CH2:29][C@H:28]([CH:43]([CH3:45])[CH3:44])[NH:27][C:26]1=[O:46])=[O:23])[C:14]([O:16]C(C)(C)C)=[O:15])=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[NH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C@H:13]([NH:21][C:22]([NH:24][C@@H:25]1[CH2:40][C:39]2=[CH:38][CH:37]=[C:36]([CH:42]=[CH:41]2)[O:35][CH2:34][CH2:33][CH2:32][CH2:31][O:30][CH2:29][C@H:28]([CH:43]([CH3:44])[CH3:45])[NH:27][C:26]1=[O:46])=[O:23])[C:14]([OH:16])=[O:15]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67320473HCID 67320473, compound

Product 1

HCID 44511932HCID 44511932, compoundYield 77.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.71 g (1.10 mmol) of tert-butyl(S)-6-tert-butoxycarbonylamino-2-[3-((9S,12R)-9-isopropyl-11-oxo-2,7-dioxa-10-azabicyclo[12.2.2]octadeca-1(17),14(18),15-trien-12-yl)ureido]hexanoate was dissolved in 11 ml of dichloromethane, and the same volume of trifluoroacetic acid was added. Stirring at RT for 4 h was followed by concentration and fractionation of the residue by preparative HPLC. The required fractions were combined and, after evaporation of acetonitrile, mixed with dilute hydrochloric acid, concentrated further and finally freeze dried. 0.42 g of the title compound was obtained as hydrochloride.

Workup

  1. concentrationwas followed by concentration and fractionation of the residue by preparative HPLC
  2. customafter evaporation of acetonitrile
  3. additionmixed with dilute hydrochloric acid
  4. concentrationconcentrated further
  5. customfinally freeze dried

Sources & evidence

ORD record
ord-bc9fa9ca64ec4187a8bf6b466399b8a2
Source dataset
uspto-grants-2014_05
Patent number
US08722655B2

Reaction notes

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