Ammonium Chloride → HCID 69211802, compound

HRID 902911Notes

Reaction equation

HRID 902911 reaction equation
[Li+].CC([N-]C(C)C)C.[CH2:9]([O:11][C:12](=[O:37])[CH2:13][CH2:14][CH2:15][CH2:16][S:17][C:18]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH3:10].Br[CH2:39][C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41].[Cl-].[NH4+]>C1COCC1.CCOCC.CN(P(N(C)C)(N(C)C)=O)C>[CH2:9]([O:11][C:12](=[O:37])[CH:13]([CH2:14][CH2:15][CH2:16][S:17][C:18]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[CH2:39][C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH3:10]

Participants

8

Reactant 4

HCID 25517Ammonium ChlorideHCID 79177tert-Butyl bromoacetateHCID 2724682Lithium diisopropylamideHCID 69224758HCID 69224758, compound

Product 1

HCID 69211802HCID 69211802, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×HCID 12679HexamethylphosphoramideSolvent

Conditions

Temperature
-40 °C

Procedure

To a solution of LDA (2M, 9.1 mL, 18.17 mmol) at −70° C. was added HMPA (10 mL) followed by the drop wise addition of a solution of the compound of example 27 (6.12 g, 15.14 mmol) in anhydrous THF (10 mL). The reaction mixture was allowed to warm up to −40° C. and was stirred for another 30 minutes, after which, a solution of tert-butyl bromoacetate (2.5 mL, 16.65 mmol) in anhydrous THF (10 mL) was added. The reaction mixture was stirred for 1 h at the same temperature and then allowed to warm up to room temperature followed by stirring for 24 h. The reaction mixture was portioned between ether and saturated ammonium chloride. The water phase was extracted several times with ether. The recombined organic layer was washed with brine, dried, filtered and evaporated. Silica gel chromatography using 5% ethyl acetate in hexanes provided the product as a light yellow oil. 1H-NMR(CDCl3, 400 MHz: 1.24(t, J=7.1 Hz, 3H); 1.43(s, 9H); 1.40-1.57(m, 4H); 2.15(m, 2H); 2.24(m, 1H); 2.58(m, 2H); 4.12(q, J=7.1 Hz, 2H), 7.19-7.23, 7.26-7.30, 7.41(m, 15H).

Workup

  1. stirringThe reaction mixture was stirred for 1 h at the same temperature
  2. temperatureto warm up to room temperature
  3. stirringby stirring for 24 h
  4. extractionThe water phase was extracted several times with ether
  5. washThe recombined organic layer was washed with brine
  6. customdried
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-6c39e74d9f7e4063870d0a2dee5cf64a
Source dataset
uspto-grants-2008_04
Patent number
US07365091B2

Reaction notes

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