1-Chloro-4-acetoxynonane → 8-Carbamoyl-12-hydroxy-13,13-dimethylheptadecanoic acid

HRID 973347Notes

Reaction equation

HRID 973347 reaction equation
ClCCCC(OC(=O)C)CCCCC.Cl[CH2:16][CH2:17][CH2:18][CH:19]([O:27]C(=O)C)[C:20]([CH3:26])([CH3:25])[CH2:21][CH2:22][CH2:23][CH3:24].C(OC(C(C)(C)CCCC)CCCC(CCCCCCC(OCC)=O)(C(OC(C)(C)C)=O)C(OC(C)(C)C)=O)(=O)C.C(C(CCCC(OC(=O)C)CCCCC(F)(F)F)CCCCCCC(OCC)=O)(O)=O.ClC(C(CCCC(OC(=O)C)CCCCC(F)(F)F)CCCCCCC(OCC)=O)=O.[C:134]([CH:137](CCCC(OC(=O)C)CCCCC(F)(F)F)[CH2:138][CH2:139][CH2:140][CH2:141][CH2:142][CH2:143][C:144]([O:146]CC)=[O:145])(=[O:136])[NH2:135].C(C(CCCC(O)CCCC(C)(C)C)CCCCCCC(O)=O)(=O)N>>[C:134]([CH:137]([CH2:16][CH2:17][CH2:18][CH:19]([OH:27])[C:20]([CH3:25])([CH3:26])[CH2:21][CH2:22][CH2:23][CH3:24])[CH2:138][CH2:139][CH2:140][CH2:141][CH2:142][CH2:143][C:144]([OH:146])=[O:145])(=[O:136])[NH2:135]

Participants

8

Reactant 7

HCID 131047161-Chloro-4-acetoxynonaneHCID 203861071-Chloro-4-acetoxy-5,5-dimethylnonaneHCID 21317557Ethyl 8carboxy-12-acetoxy-17,17,17-trifluoroheptadecanoateHCID 214016988-Carbamoyl-12-hydroxy16,16dimethylheptadecanoic acidHCID 21401740Di-tert.-butyl 2(4-acetoxy-5,5-dimethylnonyl)-2-(6-ethoxycarbonylhexyl)malonateHCID 21401748Ethyl 8-chlorocarbonyl-12-acetoxy-17,17,17-trifluoroheptadecanoateHCID 21401752Ethyl 8-carbamoyl-12-acetoxy-17,17,17-trifluoroheptadecanoate

Product 1

HCID 214017148-Carbamoyl-12-hydroxy-13,13-dimethylheptadecanoic acid

Procedure

The synthesis of this compound is carried out as described in Example 1, except that, in Step B, the 1-chloro-4-acetoxynonane is replaced by an equimolar amount of 1-chloro-4-acetoxy-5,5-dimethylnonane (Example G, Step 3). The product of Step B is thus: di-tert.-butyl 2(4-acetoxy-5,5-dimethylnonyl)-2-(6-ethoxycarbonylhexyl)malonate. Subsequent steps yield: ethyl 8-carboxy-12-acetoxy-13,13-dimethylheptadecanoate (C); ethyl 8-chlorocarbonyl-12-acetoxy-13,13-dimethylheptadecanoate (D); ethyl carbamoyl-12-acetoxy-13,13-dimethylheptadecanoate (E); and 8-carbamoyl-12-hydroxy-13,13-dimethylheptadecanoic acid (F).

Workup

  1. customThe synthesis of this compound

Sources & evidence

ORD record
ord-13be16696df2445e913a9b92e4970ccd
Source dataset
uspto-grants-1977_10
Patent number
US04055597

Reaction notes

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