(R)-2-(4-methylbenzenesulfonamido)pent-4-ynoic acid → (R)-3-(1-((R)-6-(methoxycarbonyl)-1,2,3,4-tetrahydronaphthalen-1-yl)-1H-1,2,3-triazol-4-yl)-2-(4-methylbenzenesulfonamido)propanoic acid

HRID 2219898Notes

Reaction equation

HRID 2219898 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C@H:12]([CH2:16][C:17]#[CH:18])[C:13]([OH:15])=[O:14])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[N:19]([C@@H:22]1[CH2:31][CH2:30][CH2:29][C:28]2[CH:27]=[C:26]([C:32]([O:34][CH3:35])=[O:33])[CH:25]=[CH:24][C:23]1=2)=[N+:20]=[N-:21].O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+]>CC(O)(C)C.O>[CH3:35][O:34][C:32]([C:26]1[CH:27]=[C:28]2[C:23](=[CH:24][CH:25]=1)[C@H:22]([N:19]1[CH:18]=[C:17]([CH2:16][C@@H:12]([NH:11][S:8]([C:5]3[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=3)(=[O:9])=[O:10])[C:13]([OH:15])=[O:14])[N:21]=[N:20]1)[CH2:31][CH2:30][CH2:29]2)=[O:33]

Participants

6

Reactant 3

HCID 10978432(R)-2-(4-methylbenzenesulfonamido)pent-4-ynoic acidHCID 23667548Sodium AscorbateHCID 56594895HCID 56594895, compound

Product 1

HCID 59771816(R)-3-(1-((R)-6-(methoxycarbonyl)-1,2,3,4-tetrahydronaphthalen-1-yl)-1H-1,2,3-triazol-4-yl)-2-(4-methylbenzenesulfonamido)propanoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6386tert-ButanolSolvent

Procedure

A solution of (R)-2-(4-methylbenzenesulfonamido)pent-4-ynoic acid (6.25 g, 23.4 mmol) and (R)-methyl 5-azido-5,6,7,8-tetrahydronaphthalene-2-carboxylate (5.4 g, 23.4 mmol) in 80 mL t-BuOH was treated with sodium ascorbate (0.47 g, 2.34 mmole in 24 mL H2O) and CuSO4.5H2O (0.58 g, 2.34 mmol in 24 mL H2O). An additional portion of H2O (50 mL) was then added to the reaction mixture. After stirring for 48 h at RT, the reaction mixture was diluted with H2O. A precipitate had formed that was filtered and air-dried. MS (m/z): 499.4 (m+H).

Workup

  1. customA precipitate had formed
  2. filtrationthat was filtered
  3. customair-dried

Sources & evidence

ORD record
ord-fdf3f5dfa9ff47589f95ac59970d3f48
Source dataset
uspto-grants-2008_08
Patent number
US07414134B2

Reaction notes

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