Cesium carbonate → HCID 67729725, compound

HRID 965166Notes

Reaction equation

HRID 965166 reaction equation
[C:1]([O:5][C:6](=[O:41])[CH2:7][C@H:8]([C:19](=[O:40])[NH:20][C@H:21]1[CH2:37][C:36]2=[CH:38][N:29]([C:30]3[C:35]2=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH2:28][CH2:27][O:26][CH2:25][CH2:24][NH:23][C:22]1=[O:39])[CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1)([CH3:4])([CH3:3])[CH3:2].I[CH2:43][CH2:44][CH2:45][OH:46].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[C:1]([O:5][C:6](=[O:41])[CH2:7][C@H:8]([C:19](=[O:40])[NH:20][C@H:21]1[CH2:37][C:36]2=[CH:38][N:29]([C:30]3[C:35]2=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH2:28][CH2:27][O:26][CH2:25][CH2:24][NH:23][C:22]1=[O:39])[CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:43][CH2:44][CH2:45][OH:46])=[CH:14][CH:13]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 693903-Iodo-1-propanolHCID 86752874HCID 86752874, compound

Product 1

HCID 67729725HCID 67729725, compoundYield 102.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To (3R,9S)-6-[4-hydroxyphenyl]-3-[8-oxo-4-oxa-1,7-diazatricyclo[9.6.1.012,17 ]octadeca-11(18),12,14,16-tetraen-9-ylcarbamoyl)-hexanoic acid t-butyl ester (1.0 g, 1.72 mmol) in DMF (20 mL) at 0° C. was added 3-iodopropanol(363mg, 1.95 mmol) and cesium carbonate (636 mg, 1.95 mmol). The mixture was then stirred at room temperature for 2.5 hours. DMF was removed under reduced pressure. The remaining residue was taken up in EtOAc (70 mL) and brine (40 mL). The EtOAc layer was washed with brine and dried (MgSO,). Removal of solvents to give pure (3R,9S)-6-[4-(3-hydroxy-propoxy)-phenyl]-3-[8-oxo-4-oxa-1,7-diazatricyclo[9.6.1.012,17 ]octadeca-11(18),12,14,16-tetraen-9-ylcarbamoyl)-hexanoic acid t-butyl ester (1.1 g, 100%), MS: 622.4 (M+H+).

Workup

  1. customDMF was removed under reduced pressure
  2. washThe EtOAc layer was washed with brine
  3. dry with materialdried (MgSO,)
  4. customRemoval of solvents

Sources & evidence

ORD record
ord-f584a3c30bb244b3b05405bc15a106fa
Source dataset
uspto-grants-1998_06
Patent number
US05773428

Reaction notes

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