Diisopropylethylamine → (1R,2R,5R)-tert-butyl 5-(tert-butyldiphenylsilyloxy)-2-(hex-5-enyl(methyl)carbamoyl)cyclohexanecarboxylate

HRID 926005Notes

Reaction equation

HRID 926005 reaction equation
[C:1]([O:5][C:6]([C@@H:8]1[CH2:13][C@H:12]([O:14][Si:15]([C:28]([CH3:31])([CH3:30])[CH3:29])([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:11][CH2:10][C@H:9]1[C:32](O)=[O:33])=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.S(C1C=CC(C)=CC=1)(O)(=O)=O.[CH3:68][NH:69][CH2:70][CH2:71][CH2:72][CH2:73][CH:74]=[CH2:75].C(N(C(C)C)CC)(C)C>CN(C=O)C>[Si:15]([O:14][C@H:12]1[CH2:13][C@@H:8]([C:6]([O:5][C:1]([CH3:3])([CH3:4])[CH3:2])=[O:7])[C@H:9]([C:32](=[O:33])[N:69]([CH2:70][CH2:71][CH2:72][CH2:73][CH:74]=[CH2:75])[CH3:68])[CH2:10][CH2:11]1)([C:28]([CH3:29])([CH3:31])[CH3:30])([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 46737741N-methylhex-5-en-1-amine 4-methylbenzenesulfonateHCID 58282618(1R,2R,4R)-2-(tert-butoxycarbonyl)-4-(tert-butyldiphenylsilyloxy)cyclohexanecarboxylic acid

Product 1

HCID 58282736(1R,2R,5R)-tert-butyl 5-(tert-butyldiphenylsilyloxy)-2-(hex-5-enyl(methyl)carbamoyl)cyclohexanecarboxylateYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a cold solution of compound 38 (1.80 mmol), TBTU (2.17 mmol), and N-methylhex-5-en-1-amine tosylate salt 31a (2.17 mmol) in DMF (100 mL) was added diisopropyl ethyl amine (5.4 mmol) dropwise under nitrogen at 0° C. The reaction mixture was stirred overnight at room temperature, then quenched with water and extracted with diethyl ether. The organic layer was washed with brine, then dried on magnesium sulphate, concentrated under reduced pressure, and purified by chromatography on silica gel to yield compound 39 as a beige solid in 85% yield. MS (ESI, EI+): m/z=578 (MH+).

Workup

  1. customquenched with water
  2. extractionextracted with diethyl ether
  3. washThe organic layer was washed with brine
  4. customdried on magnesium sulphate
  5. concentrationconcentrated under reduced pressure
  6. custompurified by chromatography on silica gel

Sources & evidence

ORD record
ord-10de6d2e467a4f4fbed409be22380b0b
Source dataset
uspto-grants-2016_03
Patent number
US09284307B2

Reaction notes

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