Acetic Acid → HCID 12804602, compound

HRID 223298Notes

Reaction equation

HRID 223298 reaction equation
[OH:1][C@@H:2]1[CH2:19][CH2:18][C@@:17]2([CH3:20])[C@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:16]2[C@H:15]([NH:21]C(OCC(Cl)(Cl)Cl)=O)[CH2:14][C@@:12]2([CH3:13])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C:30]([OH:32])=[O:31])[CH2:3]1.[C:33](O)(=O)C>[Zn]>[NH2:21][C@@H:15]1[CH2:14][C@@:12]2([CH3:13])[C@@H:8]([CH2:9][CH2:10][C@@H:11]2[C:30]([O:32][CH3:33])=[O:31])[C@H:7]2[C@H:16]1[C@:17]1([CH3:20])[C@@H:4]([CH2:5][CH2:6]2)[CH2:3][C@H:2]([OH:1])[CH2:19][CH2:18]1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 12804583HCID 12804583, compound

Product 1

HCID 12804602HCID 12804602, compound

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Procedure

A solution of the product of Preparation 3 (2.4 g) in glacial acetic acid (25 ml) was stirred with zinc (2.5 g) for 4 hours. The zinc was removed by filtration and washed with water (50 ml) and ether (50 ml). The filtrate and washings were brought to pH 10 with 0.88 NH3 solution and extracted with ester (×4). The extract was washed with water, dried and evaporated to leave a solid (1.65 g). A portion was crystallised from ether to give the title compound, m.p. 113°-116°, [α]D +38°

Workup

  1. customThe zinc was removed by filtration
  2. washwashed with water (50 ml) and ether (50 ml)
  3. extractionextracted with ester (×4)
  4. washThe extract was washed with water
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-0e3db53bc04e4808a510fc476bf7d831
Source dataset
uspto-grants-1982_10
Patent number
US04352798

Reaction notes

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