Water → HCID 70446069, compound

HRID 1731510Notes

Reaction equation

HRID 1731510 reaction equation
[Br-].[CH3:2][C:3]1([CH3:30])[CH2:7][CH2:6][C:5]([CH3:9])([CH3:8])[CH:4]1[CH2:10][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C([Li])(CC)C.[CH2:36]([O:43][C:44]([C:46]([NH2:59])([C:49]([O:51][CH2:52][C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1)=[O:50])[CH:47]=O)=[O:45])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.O>O1CCCC1.C1CCCCC1>[C:49]([C:46]([NH2:59])([CH:47]=[CH:10][CH:4]1[C:5]([CH3:8])([CH3:9])[CH2:6][CH2:7][C:3]1([CH3:2])[CH3:30])[C:44]([O:43][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)=[O:45])([O:51][CH2:52][C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1)=[O:50]

Participants

7

Reactant 4

HCID 962WaterHCID 86740921HCID 86740921, compoundHCID 86740923HCID 86740923, compoundHCID 178418400CID 53628100

Product 1

HCID 70446069HCID 70446069, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8078CyclohexaneSolvent

Procedure

The 2,2,5,5-tetramethyl cyclopentylmethyl triphenylphosphonium bromide is suspended in tetrahydrofuran at 0° C. under argon. Sec-Butyllithium in cyclohexane is added followed by a solution of 2-benzyloxycarbonyl-2-CBZ-aminoacetaldehyde in tetrahydrofuran. After one hour, water is added to the reaction mixture. The organic layer is separated, washed with water and dried over MgSO4 and evaporated to yield the alkene, benzyl 2-CBZ-amino-4-(2,2,5,5-tetramethylcyclopentyl)-3-butenoate.

Workup

  1. customThe organic layer is separated
  2. washwashed with water
  3. dry with materialdried over MgSO4
  4. customevaporated

Sources & evidence

ORD record
ord-11cc6a0f7d324422a11a8a79bc87c34d
Source dataset
uspto-grants-1986_11
Patent number
US04622232

Reaction notes

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