Citric Acid → HCID 67382508, compound

HRID 1429412Notes

Reaction equation

HRID 1429412 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][C@H:5]([N:13]([CH2:28][C:29]([OH:31])=O)[S:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[O:23][C:24]([F:27])([F:26])[F:25])(=[O:16])=[O:15])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.CCN(C(C)C)C(C)C.C1N(P(Cl)(N2C(=O)OCC2)=O)C(=O)OC1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(Cl)Cl>[CH2:6]([C@@H:5]1[CH2:4][CH2:3][CH2:2][NH:1][C:29](=[O:31])[CH2:28][N:13]1[S:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[O:23][C:24]([F:25])([F:26])[F:27])(=[O:15])=[O:16])[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 311Citric AcidHCID 81531DiisopropylethylamineHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 71269357(S)-2-(N-(5-Amino-1-phenylpentan-2-yl)-2-(trifluoromethoxy)phenylsulfonamido)acetic acid

Product 1

HCID 67382508HCID 67382508, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of compound 31l (2.3 g, 5.0 mmol) in DCM (50 mL) was added DIPEA (2.6 g, 20 mmol) and BOP-Cl (1.5 g, 6.0 mmol). The reaction mixture was stirred at rt for 5 h under nitrogen, then 50 mL DCM and 10% citric acid were added to the mixture. The organic layer was separated, washed with brine and dried over anhydrous Na2SO4. After filtration, the filtrate was evaporated and the residue was purified by CC (hexane/EA=3:1) to give compound 31m (1.9 g, 88% yield).

Workup

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationAfter filtration
  5. customthe filtrate was evaporated
  6. customthe residue was purified by CC (hexane/EA=3:1)

Sources & evidence

ORD record
ord-ff245f783b62440cab498cdd3e45e389
Source dataset
uspto-grants-2015_01
Patent number
US08940722B2

Reaction notes

Loading…