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 2040023Notes

Reaction equation

HRID 2040023 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-3a461e79d838409699e06dfa8df18326
Source dataset
uspto-grants-2013_11
Patent number
US08580777B2

Reaction notes

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