tert-Butyl (S)-6-tert-butoxycarbonylamino-2-[((9S,12R)-9-isopropyl-11-oxo-2,7-dioxa-10-azabicyclo[12.2.2]octadeca-1(17),14(18),15-trien-12-ylsulfamoyl)amino]hexanoate → (S)-6-Amino-2-[((9S,12R)-9-isopropyl-11-oxo-2,7-dioxa-10-azabicyclo[12.2.2]octadeca-1(17),14(18),15-trien-12-ylsulfamoyl)amino]hexanoic acid

HRID 2274558Notes

Reaction equation

HRID 2274558 reaction equation
C(OC([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][C@H:13]([NH:21][S:22](=[O:47])(=[O:46])[NH:23][C@@H:24]1[CH2:39][C:38]2=[CH:40][CH:41]=[C:35]([CH:36]=[CH:37]2)[O:34][CH2:33][CH2:32][CH2:31][CH2:30][O:29][CH2:28][C@H:27]([CH:42]([CH3:44])[CH3:43])[NH:26][C:25]1=[O:45])[C:14]([O:16]C(C)(C)C)=[O:15])=O)(C)(C)C>ClCCl.C(O)(C(F)(F)F)=O>[NH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C@H:13]([NH:21][S:22](=[O:46])(=[O:47])[NH:23][C@@H:24]1[CH2:39][C:38]2=[CH:37][CH:36]=[C:35]([CH:41]=[CH:40]2)[O:34][CH2:33][CH2:32][CH2:31][CH2:30][O:29][CH2:28][C@H:27]([CH:42]([CH3:44])[CH3:43])[NH:26][C:25]1=[O:45])[C:14]([OH:16])=[O:15]

Participants

3

Reactant 1

HCID 67320439tert-Butyl (S)-6-tert-butoxycarbonylamino-2-[((9S,12R)-9-isopropyl-11-oxo-2,7-dioxa-10-azabicyclo[12.2.2]octadeca-1(17),14(18),15-trien-12-ylsulfamoyl)amino]hexanoate

Product 1

HCID 67320445(S)-6-Amino-2-[((9S,12R)-9-isopropyl-11-oxo-2,7-dioxa-10-azabicyclo[12.2.2]octadeca-1(17),14(18),15-trien-12-ylsulfamoyl)amino]hexanoic acidYield 56.4%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A solution of 78 mg (0.114 mmol) of tert-butyl (S)-6-tert-butoxycarbonylamino-2-[((9S,12R)-9-isopropyl-11-oxo-2,7-dioxa-10-azabicyclo[12.2.2]octadeca-1(17),14(18),15-trien-12-ylsulfamoyl)amino]hexanoate in 3 ml of dichloromethane/TFA (1:1, v/v) was left to stand at RT for 2 h and then concentrated. The crude product was purified by prep. HPLC. The required fractions were combined and freeze dried after addition of 1N hydrochloric acid. 34 mg of the title compound were obtained as hydrochloride. LC/MS (method F): Rt=2.97 min, m/z: 529.23 [MH+].

Workup

  1. concentrationconcentrated
  2. customThe crude product was purified by prep
  3. customfreeze dried
  4. additionafter addition of 1N hydrochloric acid

Sources & evidence

ORD record
ord-cc28ec0391c3407ab8f3d36001f1dd9b
Source dataset
uspto-grants-2015_09
Patent number
US09126955B2

Reaction notes

Loading…