Imidazole → HCID 59383062, compound

HRID 451860Notes

Reaction equation

HRID 451860 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:14][CH:15]1[CH2:20][CH2:19][CH:18]([OH:21])[CH2:17][CH2:16]1)[C:10]([O:12][CH3:13])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].N1C=CN=C1.[CH3:27][C:28]([Si:31](Cl)([CH3:33])[CH3:32])([CH3:30])[CH3:29].O>C(Cl)Cl>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:14][CH:15]1[CH2:20][CH2:19][CH:18]([O:21][Si:31]([C:28]([CH3:30])([CH3:29])[CH3:27])([CH3:33])[CH3:32])[CH2:17][CH2:16]1)[C:10]([O:12][CH3:13])=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 59383042HCID 59383042, compound

Product 1

HCID 59383062HCID 59383062, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the (S)-methyl 2-(tert-butoxycarbonylamino)-3-(4-hydroxycyclohexyl)propanoate (96.56 g, 0.32 mol) in CH2Cl2 (500 mL) was added imidazole (43.52 g, 0.64 mol), followed by TBSCl (72 g, 0.48 mol) at 0° C. After addition, the mixture was allowed to stir at rt overnight. The reaction mixture was treated with water and extracted with CH2Cl2. The organic layer was dried over Na2SO4, filtered, and evaporated to give (S)-methyl 2-(tert-butoxycarbonylamino)-3-(4-(tert-butyldimethylsilyloxy)cyclohexyl)propanoate (133 g, yield 100%). 1H NMR: (CDCl3, 400 MHz) δ 0.08 (d, 6H), 0.89 (d, 9H), 1.45 (s, 9H), 1.51 (m, 4H), 1.58 (m, 1H), 1.68 (t, 4H), 1.85 (d, 1H), 3.71 (d, 3H), 3.91 (m, 1H), 4.34 (m, 1H), 4.86 (m, 1H).

Workup

  1. additionAfter addition
  2. extractionextracted with CH2Cl2
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-1f53ef2ad2074e768765df55e32b7f37
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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