Diisobutylaluminum hydride → HCID 59771820, compound

HRID 2219900Notes

Reaction equation

HRID 2219900 reaction equation
[NH2:1][C:2](=[O:34])[C@H:3]([NH:23][S:24]([C:27]1[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=1)(=[O:26])=[O:25])[CH2:4][C:5]1[N:6]=[N:7][N:8]([C@@H:10]2[CH2:19][CH2:18][CH2:17][C:16]3[CH:15]=[C:14]([C:20](O)=[O:21])[CH:13]=[CH:12][C:11]2=3)[CH:9]=1.CC(C[AlH]CC(C)C)C>C1(C)C=CC=CC=1>[OH:21][CH2:20][C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][CH:13]=1)[C@H:10]([N:8]1[CH:9]=[C:5]([CH2:4][C@@H:3]([NH:23][S:24]([C:27]3[CH:28]=[CH:29][C:30]([CH3:33])=[CH:31][CH:32]=3)(=[O:25])=[O:26])[C:2]([NH2:1])=[O:34])[N:6]=[N:7]1)[CH2:19][CH2:18][CH2:17]2

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 59771819HCID 59771819, compound

Product 1

HCID 59771820HCID 59771820, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirred solution of (R)-5-(4-((R)-3-amino-2-(4-methylbenzenesulfonamido)-3-oxopropyl)-1H-1,2,3-triazol-1-yl)-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid (1.63 g, 3.28 mmol) in 40 mL toluene was added a solution of 1.5M DIBAL-H in toluene. The reaction mixture was stirred for 3 h and then cooled to 0° C. The reaction mixture was quenched by the slow addition of 10% HCl and extracted with EtOAc (3×). The extracts were dried over MgSO4, concentrated and purified by Sio2 (5% MeOH/CH2Cl2) to afford a light yellow solid. MS (m/z): 470.4 (m+H).

Workup

  1. customThe reaction mixture was quenched by the slow addition of 10% HCl
  2. extractionextracted with EtOAc (3×)
  3. dry with materialThe extracts were dried over MgSO4
  4. concentrationconcentrated
  5. custompurified by Sio2 (5% MeOH/CH2Cl2)
  6. customto afford a light yellow solid

Sources & evidence

ORD record
ord-a4789c61ab214b4ab4a5be3e22bc6447
Source dataset
uspto-grants-2008_08
Patent number
US07414134B2

Reaction notes

Loading…