Ethyl 7-bromoheptanoate → 8-Carbamoyl-12-hydroxy-3-methylheptadecanoic acid

HRID 973351Notes

Reaction equation

HRID 973351 reaction equation
BrCCCCCCC(OCC)=O.[CH3:13][CH:14]([CH2:20][CH2:21][CH2:22][CH2:23]I)[CH2:15][C:16]([O:18]C)=[O:17].COC(CC(C)CCCCC(C(OC(C)(C)C)=O)C(OC(C)(C)C)=O)=O.C(OC(CCCCC)CCCC(CCCCC(C)CC(OC)=O)(C([O-])=O)C(OC(C)(C)C)=O)(=O)C.C(C(CCCC(OC(=O)C)CCCCC)CCCCC(C)CC(OC)=O)(O)=O.[C:114]([CH:117]([CH2:129][CH2:130][CH2:131][C@@H:132]([O:138]C(=O)C)[CH2:133][CH2:134][CH2:135][CH2:136][CH3:137])CCCCCCC(OCC)=O)(=[O:116])[NH2:115].C(C(CCCCCC(C(=O)N)CCC[C@@H](O)CCCCC)C(O)=O)C>>[C:114]([CH:117]([CH2:129][CH2:130][CH2:131][CH:132]([OH:138])[CH2:133][CH2:134][CH2:135][CH2:136][CH3:137])[CH2:23][CH2:22][CH2:21][CH2:20][CH:14]([CH3:13])[CH2:15][C:16]([OH:18])=[O:17])(=[O:116])[NH2:115]

Participants

8

Reactant 7

HCID 122490Ethyl 7-bromoheptanoateHCID 20322201Methyl 3-methyl-7-iodoheptanoateHCID 22799886ethyl 8-carbamoyl-12-(S)-hydroxyheptadecanoic acidHCID 53657493Methyl 8carboxy-12-acetoxy-3-methylheptadecanoateHCID 54170379ethyl 8-carbamoyl-12-(S)-acetoxyheptadecanoateHCID 86735176Di-tert.-butyl (6-methoxycarbonyl-5-methylhexyl)malonateHCID 86735177Tert.-butyl 2-(4-acetoxynonyl)-2-(6-methoxycarbonyl-5-methylhexyl)malonate2×

Product 1

HCID 214017048-Carbamoyl-12-hydroxy-3-methylheptadecanoic acid

Procedure

The synthesis of this compound is carried out as described in Example 1 except that, in Step A, the ethyl 7-bromoheptanoate is replaced by an equimolar amount of methyl 3-methyl-7-iodoheptanoate. The product of Step A is thus: di-tert.-butyl (6-methoxycarbonyl-5-methylhexyl)malonate. Subsequent steps yield: di.-tert.-butyl 2-(4-acetoxynonyl)-2-(6-methoxycarbonyl-5-methylhexyl)malonate (D); methyl 8carboxy-12-acetoxy-3-methylheptadecanoate (V); methyl 8-chlorocarbonyl-12-acetoxy-3-methylheptadecanoate (D); methyl 8-carbamoyl-12-acetoxy-3-methylheptadecanote (E); and 8carbamoyl-12-acetoxy-3-methylheptadecanoic acid (F).

Workup

  1. customThe synthesis of this compound

Sources & evidence

ORD record
ord-f5ad0926191d484091dc4ea1e159b25c
Source dataset
uspto-grants-1977_10
Patent number
US04055597

Reaction notes

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