Dicyclohexylcarbodiimide → HCID 46840707, compound
Reaction equation
C1CCC(N=C=NC2CCCCC2)CC1.Cl.[CH3:17][S:18][C:19]1[CH:20]=[C:21]([NH:25][CH:26]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:27]([OH:29])=[O:28])[CH:22]=[CH:23][CH:24]=1.C1C=CC2N(O)N=NC=2C=1.[N:46]12[CH2:53][CH2:52][CH:49]([CH2:50][CH2:51]1)[C@@H:48](O)[CH2:47]2>C1COCC1>[N:46]12[CH2:53][CH2:52][CH:49]([CH2:50][CH2:51]1)[C@@H:48]([O:28][C:27](=[O:29])[CH:26]([NH:25][C:21]1[CH:22]=[CH:23][CH:24]=[C:19]([S:18][CH3:17])[CH:20]=1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH2:47]2Participants
6
Procedure
PS-DCC (602 mg, 0.80 mmol, loading: 1.33 mmol/g) is suspended in dry THF (15 mL). (3-Methylsulfanyl-phenylamino)-phenyl-acetic acid hydrochloride (I51) (124 mg, 0.40 mmol), HOBT (123 mg, 0.80 mmol), and (R)-quinuclidin-3-ol (153 mg, 1.20 mmol) are added and the suspension is shaken at RT overnight (16 hours). PS-DCC is filtered off, washed with THF and the filtrate is evaporated. The resulting residue is dissolved in EtOAc and washed with sat. NaHCO3, water and brine. The organic layer is recovered, dried over Na2SO4, filtered and evaporated to afford the title compound as a brown oil (153 mg, quantitative yield, mixture of diastereoisomers).
Workup
- filtrationPS-DCC is filtered off
- washwashed with THF
- customthe filtrate is evaporated
- dissolutionThe resulting residue is dissolved in EtOAc
- washwashed with sat. NaHCO3, water and brine
- customThe organic layer is recovered
- dry with materialdried over Na2SO4
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-424548cc701c45788e8aa443e173eed4
- Source dataset
- uspto-grants-2013_06
- Patent number
- US08455646B2
Reaction notes
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