Di-tert.-butyl 2-[4-(2-tetrahydropyranyloxy)nonyl]-2-(6-ethoxycarbonylhexyl)malonate → 8-Carbamoyl-12-(R)-hydroxyheptadecanoic Acid

HRID 973350Notes

Reaction equation

HRID 973350 reaction equation
O1CCCCC1[O:7][C@@H:8]([CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[CH2:9][CH2:10][CH2:11][C:12]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]([O:31]CC)=[O:30])(C([O-])=O)[C:13](OC(C)(C)C)=[O:14].CS(OCCC[C@@H](OC1CCCCO1)CCCCC)(=O)=O.CS(OCCC[C@H](OC1CCCCO1)CCCCC)(=O)=O.O1CCCCC1OC(CCCCC)CCCC(CCCCCCC(OCC)=O)(C(OC(C)(C)C)=O)C(OC(C)(C)C)=O.O[C@H](CCCCC)CCCC(CCCCCCC(OCC)=O)(C(OC(C)(C)C)=O)C(OC(C)(C)C)=O.C(O[C@H](CCCCC)CCCC(CCCCCCC(OCC)=O)(C(OC(C)(C)C)=O)C(OC(C)(C)C)=O)(=O)C.C(C(CCC[C@@H](OC(=O)C)CCCCC)CCCCCCC(OCC)=O)(O)=O.ClC(C(CCC[C@@H](OC(=O)C)CCCCC)CCCCCCC(OCC)=O)=O.C(C(CCC[C@@H](OC(=O)C)CCCCC)CCCCCCC(OCC)=O)(=O)[NH2:255].C(C(CCCCCC(C(=O)N)CCC[C@@H](O)CCCCC)C(O)=O)C>>[C:13]([CH:12]([CH2:11][CH2:10][CH2:9][C@H:8]([OH:7])[CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]([OH:31])=[O:30])(=[O:14])[NH2:255]

Participants

11

Reactant 10

HCID 21401741Di-tert.-butyl 2-[4-(2-tetrahydropyranyloxy)nonyl]-2-(6-ethoxycarbonylhexyl)malonateHCID 22799882di-tert.-butyl 2-(4-(R)-hydroxynonyl)-2-(6ethoxycarbonylhexyl)malonateHCID 22799886ethyl 8-carbamoyl-12-(S)-hydroxyheptadecanoic acidHCID 53853233ethyl 8-carboxy-12-(S)-acetoxyheptadecanoateHCID 53958578(4R)-1-methylsulfonyloxy-4-(2-tetrahydropyranyloxy)nonaneHCID 54106387ethyl 8-chlorocarbonyl-12-(S)-acetoxyheptadecanoateHCID 54170379ethyl 8-carbamoyl-12-(S)-acetoxyheptadecanoateHCID 86735174(4S)-1-methylsulfonyloxy-4-(2-tetrahydropyranyloxy)-nonaneHCID 86735175di-tert.-butyl 2-(4-(R)-acetoxynonyl)-2-(6-ethoxycarbonylhexyl)malonateHCID 131710945tert.-butyl 2-[4-(S)-(2-tetrahydropyranyloxy)-nonyl]-2-(ethoxycarbonylhexyl)malonate

Product 1

HCID 227998808-Carbamoyl-12-(R)-hydroxyheptadecanoic Acid

Procedure

The synthesis of this compound is carried out exactly according to the procedure described for the 12-(S) compound of Example 13 except that in Step B, the (4S)-1-methylsulfonyloxy-4-(2-tetrahydropyranyloxy)-nonane is replaced by an equimolar amount of (4R)-1-methylsulfonyloxy-4-(2-tetrahydropyranyloxy)nonane (Example I, Step 7). The product of Step B is thus di-tert.-butyl 2-[4-(2-tetrahydropyranyloxy)nonyl]-2-(6-ethoxycarbonylhexyl)malonate. Subsequent steps yield: di-tert.-butyl 2-(4-(R)-hydroxynonyl)-2-(6ethoxycarbonylhexyl)malonate (B-1); di-tert.-butyl 2 -(4-(R)-acetoxynonyl)-2-(6-ethoxycarbonylhexyl)malonate (B-2); ethyl 8-carboxy-12-(R)-acetoxyheptadecanoate (C); ethyl 8-chlorocarbonyl-12-(R)-acetoxyheptadecanoate (D); ethyl 8-carbamoyl-12-(R)-acetoxyheptadecanoate (E); and 8-carbamoyl-12-(R)-hydroxheptadecanoic acid (F).

Workup

  1. customThe synthesis of this compound

Sources & evidence

ORD record
ord-969cf781dd384466a48d67cdb933fd47
Source dataset
uspto-grants-1977_10
Patent number
US04055597

Reaction notes

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