Ammonium Chloride → HCID 22977309, compound

HRID 412488Notes

Reaction equation

HRID 412488 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH2:11]([O:18][C:19]([NH:21][C:22]1[CH:23]=[C:24]2[C:28](=[CH:29][CH:30]=1)[N:27]([C:31]([C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[N:26]=[CH:25]2)=[O:20])[C:12]1C=CC=CC=1.[C:50](OC[C@@H]1OC1)(=[O:54])CCC.[NH4+].[Cl-]>O1CCCC1>[OH:54][CH2:50][C@@H:11]1[O:18][C:19](=[O:20])[N:21]([C:22]2[CH:23]=[C:24]3[C:28](=[CH:29][CH:30]=2)[N:27]([C:31]([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)([C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[N:26]=[CH:25]3)[CH2:12]1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 2724536(2R)-Oxiran-2-ylmethyl butanoateHCID 2733832Lithium HexamethyldisilazideHCID 22245080HCID 22245080, compound

Product 1

HCID 22977309HCID 22977309, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1 M Lithium bis(trimethylsilyl)amide in tetrahydrofuran (1.1 mL, 1.1 mmol) was added dropwise with stirring at −78° C. to 5-benzyloxycarbonylamino-1-tritylindazole (0.510 g, 1 mmol) in tetrahydrofuran (10 mL) under nitrogen atmosphere. The mixture was stirred at −78° C. for 1.5 h. (R)-Glycidyl butyrate (0.160 mL, 1.2 mmol) was added dropwise with stirring. The mixture was allowed to warm to r.t. overnight. Saturated aq. NH4Cl (10 mL) was added, and the mixture was extracted with EtOAc (2×20 mL). The combined organic layers were washed with water (10 mL), brine (10 mL), and dried (MgSO4). Solvent was evaporated to 3 mL, and the residue was triturated with hexanes (50 mL). White crystalline product was filtered off, washed with hexanes, and dried in vacuo. Yield 0.440 g (93%). MS (m/z): 232.1 [M-Trt]−. 1H NMR.

Workup

  1. additionwas added dropwise
  2. extractionthe mixture was extracted with EtOAc (2×20 mL)
  3. washThe combined organic layers were washed with water (10 mL), brine (10 mL)
  4. dry with materialdried (MgSO4)
  5. customSolvent was evaporated to 3 mL
  6. customthe residue was triturated with hexanes (50 mL)
  7. filtrationWhite crystalline product was filtered off
  8. washwashed with hexanes
  9. customdried in vacuo

Sources & evidence

ORD record
ord-73abbc97f8584cab9ae8e6c2d4faca50
Source dataset
uspto-grants-2003_05
Patent number
US06562844B2

Reaction notes

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