Hydrochloric Acid → HCID 51031005, compound

HRID 1844650Notes

Reaction equation

HRID 1844650 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][S:5][S:6][CH2:7][CH2:8][NH:9][C:10](=[O:18])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[OH:17].[CH2:19]1[C@@H:23]([CH2:24][CH2:25][CH2:26][CH2:27][C:28](O)=[O:29])[S:22][S:21][CH2:20]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O>[S:21]1[CH2:20][CH2:19][C@H:23]([CH2:24][CH2:25][CH2:26][CH2:27][C:28]([NH:2][CH2:3][CH2:4][S:5][S:6][CH2:7][CH2:8][NH:9][C:10](=[O:18])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[OH:17])=[O:29])[S:22]1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 6112Lipoic acidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58218979N-(2-(2-(2-aminoethyl)-disulfanyl)-ethyl)-2-hydroxybenzamide

Product 1

HCID 51031005HCID 51031005, compoundYield 24%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

The HCl salt of N-(2-(2-(2-aminoethyl)-disulfanyl)-ethyl)-2-hydroxybenzamide (0.322 mmol) was taken up in DMF (5 mL) along with (R)-α-lipoic acid (TCI, 66 mg, 0.322 mmol) HATU (134 mg, 0.354 mmol) and DIEA (170 μL, 0.97 mmol). The resulting reaction mixture was stirred at room temperature for 4 h. It was then diluted with EtOAc (30 mL) and washed successively with water (3×5 mL) and brine. The organic layer was dried over Na2SO4 and concentrated under reduced pressure. Purification by chromatography (CH2Cl2) afforded (S)—N-(2-(2-(2-(5-(1,2-dithiolan-3-yl)pentanamido)ethyl)disulfanyl)ethyl)-2-hydroxybenzamide (35 mg, 24%). Mass calculated for C19H28N2O3S4: 460.1. found: [M+H]+=461.

Workup

  1. customThe resulting reaction mixture
  2. washwashed successively with water (3×5 mL) and brine
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customPurification by chromatography (CH2Cl2)

Sources & evidence

ORD record
ord-f2d131f6a3c94a0a84050d7efa74ada9
Source dataset
uspto-grants-2015_02
Patent number
US08946451B2

Reaction notes

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