Potassium Carbonate → HCID 91130494, compound

HRID 2377266Notes

Reaction equation

HRID 2377266 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([C:37]2[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[CH:39][CH:38]=2)[N:10]2[C:14]3[C:15]4[C:20]([CH2:21][C:13]=3[C:12]([C:30]3[S:34][C:33]([CH2:35]O)=[CH:32][CH:31]=3)=[N:11]2)=[CH:19][C:18]([CH2:22][N:23]2[CH2:28][CH2:27][N:26]([CH3:29])[CH2:25][CH2:24]2)=[CH:17][CH:16]=4)=[CH:5][CH:4]=1.C1(P([N:59]=[N+:60]=[N-:61])(C2C=CC=CC=2)=O)C=CC=CC=1.N12CCCN=C1CCCCC2.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1>[N:59]([CH2:35][C:33]1[S:34][C:30]([C:12]2[C:13]3[CH2:21][C:20]4[C:15](=[CH:16][CH:17]=[C:18]([CH2:22][N:23]5[CH2:24][CH2:25][N:26]([CH3:29])[CH2:27][CH2:28]5)[CH:19]=4)[C:14]=3[N:10]([CH:9]([C:6]3[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[C:37]3[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[CH:39][CH:38]=3)[N:11]=2)=[CH:31][CH:32]=1)=[N+:60]=[N-:61]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 69202369HCID 69202369, compound

Product 1

HCID 91130494HCID 91130494, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of Example 382 (8.0 g, 13.2 mmol) in tetrahydrofuran (100 mL) was cooled to about 0° C. and diphenylphosphoryl azide (7.1 mL, 33.0 mmol) followed by 1,8-diazabicyclo[5.4.0]undec-7ene (4.9 mL, 33.0 mmol) were added slowly in the dark. After the addition was complete, the mixture was stirred for about 2 hours at ambient temperature in the dark. The mixture was basified by addition of potassium carbonate and concentrated under vacuum. The residue was diluted with water, extracted with ethyl acetate and the combined organic extracts were dried (MgSO4), filtered, and concentrate. The residue was purified by flash chromatography on silica gel using dichloromethane/methanol (10:1) as eluent to provide the desired product. MS (ESI): m/z 632 (M+H)+.

Workup

  1. additionwere added slowly in the dark
  2. additionAfter the addition
  3. concentrationconcentrated under vacuum
  4. additionThe residue was diluted with water
  5. extractionextracted with ethyl acetate
  6. dry with materialthe combined organic extracts were dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrate
  9. customThe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-82342cfba081446a9e79aa644ea7582a
Source dataset
uspto-grants-2008_12
Patent number
US07468371B2

Reaction notes

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