Triethylamine → HCID 44434808, compound
Reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:9][C@H:10]2[C@@H:14]([NH:15][C:16](=[O:30])[C:17]3[CH:22]=[CH:21][C:20]([N:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]4=[O:29])=[CH:19][CH:18]=3)[CH2:13][C@H:12]([C:31](O)=[O:32])[CH2:11]2)=[O:8])=[CH:4][CH:3]=1.CCN(CC)CC.ClC(OCC)=O.[BH4-].[Na+]>C1COCC1.CCOC(C)=O>[OH:32][CH2:31][C@@H:12]1[CH2:11][C@@H:10]([NH:9][C:7]([C:5]2[S:6][C:2]([Cl:1])=[CH:3][CH:4]=2)=[O:8])[C@@H:14]([NH:15][C:16](=[O:30])[C:17]2[CH:22]=[CH:21][C:20]([N:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]3=[O:29])=[CH:19][CH:18]=2)[CH2:13]1Participants
Conditions
- Temperature
- 0 °C
Procedure
The product from Example 94 (0.22 g, 0.45 mmol) was stirred in THF (10 mL) at 0° C., Et3N (0.095 mL, 0.68 mmol, 1.5 eq) was added followed by dropwise addition of ClCOOEt (0.051 mL, 0.54 mmol, 1.2 eq). The mixture was stirred at 0° C. for 1 h. It was filtered and rinsed with THF (10 mL). The THF solution was stirred at 0° C. MeOH (5 mL) was added followed by addition of NaBH4 (0.25 mg, 6.6 mmol). The resulting mixture was stirred at 0° C. for 1 h. LC/MS showed completion of the reaction. EtOAc was added, it was washed with NH4Cl, H2O, and brine. The organic layer was concentrated, and purified by reverse phase HPLC (MeOH/H2O in 0.1% TFA) to give pure title compound. LC-MS (ESI) 472.12, 474.04 (M+H), 488.06 (M+Na), tR=2.54 min (10–90% MeOH in H2O with 0.1% TFA in a 4-min run).
Workup
- filtrationIt was filtered
- washrinsed with THF (10 mL)
- stirringThe THF solution was stirred at 0° C
- additionMeOH (5 mL) was added
- stirringThe resulting mixture was stirred at 0° C. for 1 h
- customcompletion of the reaction
- washit was washed with NH4Cl, H2O, and brine
- concentrationThe organic layer was concentrated
- custompurified by reverse phase HPLC (MeOH/H2O in 0.1% TFA)
Sources & evidence
- ORD record
- ord-34fd9ba687dc4da7a2589c0f6da0aa4c
- Source dataset
- uspto-grants-2007_04
- Patent number
- US07205318B2
Reaction notes
Loading…