Dicyclohexylcarbodiimide → HCID 59401188, compound

HRID 76971

Reaction equation

HRID 76971 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C1CCC(N=C=NC2CCCCC2)CC1.C1C=CC2N(O)N=NC=2C=1.[N:45]12[CH2:52][CH2:51][CH:48]([CH2:49][CH2:50]1)[C@@H:47](O)[CH2:46]2>C1COCC1>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:10]([O:12][C@@H:47]1[CH:48]2[CH2:51][CH2:52][N:45]([CH2:50][CH2:49]2)[CH2:46]1)=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 77857L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-HCID 914043-Quinuclidinol, (-)-

Product 1

HCID 59401188HCID 59401188, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-2-(tert-butoxycarbonylamino)-3-phenylpropanoic acid (1.03 g, 3.81 mmol) in THF (70 mL), are added DCC (1.03 g, 4.91 mmol), HOBt (660 mg, 4.90 mmol) and 3(R)-quinuclidinol (1.18 g, 9.48 mmol) and the resulting mixture is stirred for 12 hours at RT under nitrogen flowstream (LC-MS monitoring: complete conversion). The solvent is evaporated and the residue is partitioned between EtOAc (100 mL) and 2M K2CO3 (50 mL); the organic layer is separated, washed with brine and dried over Na2SO4. The resulting crude is purified by flash chromatography (DCM/MeOH=95/5, 0.1% NH3 (aq.)) to obtain 1.12 g of I19 (80% yield).

Workup

  1. customThe solvent is evaporated
  2. customthe residue is partitioned between EtOAc (100 mL) and 2M K2CO3 (50 mL)
  3. customthe organic layer is separated
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. customThe resulting crude is purified by flash chromatography (DCM/MeOH=95/5, 0.1% NH3 (aq.))
  7. customto obtain 1.12 g of I19 (80% yield)

Sources & evidence

ORD record
ord-0857f016133b479ea8a06b8bbeb5fae3
Source dataset
uspto-grants-2014_09
Patent number
US08835682B2

Linked notes

Loading…