Acetic Acid → HCID 12804602, compound

HRID 544639Notes

Reaction equation

HRID 544639 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 ether (×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 ether (×4)
  4. washThe extract was washed with water
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-45165c74966b4675abf0b3a28128c682
Source dataset
uspto-grants-1984_05
Patent number
US04451405

Reaction notes

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