Triethylamine → HCID 86748874, compound

HRID 1755814Notes

Reaction equation

HRID 1755814 reaction equation
[NH2:1][C@H:2]([C:4]1[CH2:9][CH:8]=[C:7]([O:10][CH3:11])[CH2:6][CH:5]=1)[CH3:3].[CH2:12]([O:19][C:20](ON1C(=O)CCC1=O)=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(CC)CC)C>C1COCC1>[CH2:12]([O:19][C:20]([NH:1][C@H:2]([C:4]1[CH2:9][CH:8]=[C:7]([O:10][CH3:11])[CH2:6][CH:5]=1)[CH3:3])=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 83172Benzyl succinimido carbonateHCID 54552279HCID 54552279, compound

Product 1

HCID 86748874HCID 86748874, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of the above diene (31) in THF (250 mL) was added in one portion N-(benzyloxycarbonyloxy) -succinimide (40 g) (slightly exothermic) followed by after 15 min triethylamine (23 mL). The reaction was stirred for 16 h at room temperature, evaporated, taken up in ethyl acetate, washed with 1N Na2CO3, saturated NaCl, dried over MgSO4 and evaporated to give crude product (32). TLC Rf 0.26 (10% ethyl acetate, n-hexane); 1H NMR (CDCl3) δ1.24 (3H, d, J=7 Hz), 2.73(4H, br s), 3.55(3H, s), 4.27(1H, q), 4.64(1H, br s), 4.78(1H, br d), 5.12(2H, s), 5.64(1H, br s), 7.38 (5H, s).

Workup

  1. customafter 15 min
  2. customevaporated
  3. washwashed with 1N Na2CO3, saturated NaCl
  4. dry with materialdried over MgSO4
  5. customevaporated

Sources & evidence

ORD record
ord-e85f2d00d5874547bbcd7aec16cf52b9
Source dataset
uspto-grants-1995_08
Patent number
US05438118

Reaction notes

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