Piperidine → HCID 454704, compound

HRID 1456923Notes

Reaction equation

HRID 1456923 reaction equation
C[N+:2]([CH2:5][CH2:6][O:7][P:8]([O:11][CH2:12][C@H:13]([O:31][C:32]([CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][O:45][CH3:46])=[O:33])[CH2:14][O:15][C:16]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][O:29][CH3:30])=[O:17])([OH:10])=[O:9])(C)C.C[N+](CCOP(OC[C@H](OC(CCCCCCCCCCCOC)=O)COC(CCCCCCCCCCCOC)=O)([O-])=O)(C)C.C1C2C(COC(ON3C(=O)CCC3=O)=O)C3C(=CC=CC=3)C=2C=CC=1.N1CCCCC1.C(OC(=O)CCCCCCCCCCCCC)(=O)CCCCCCCCCCCCC>>[CH3:30][O:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][C:16]([O:15][CH2:14][C@H:13]([O:31][C:32]([CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][O:45][CH3:46])=[O:33])[CH2:12][O:11][P:8]([O:7][CH2:6][CH2:5][NH2:2])([OH:10])=[O:9])=[O:17]

Participants

6

Reactant 5

HCID 8082PiperidineHCID 69377Tetradecanoic anhydrideHCID 134122N-(9-Fluorenylmethoxycarbonyloxy)succinimideHCID 454703HCID 454703, compoundHCID 30813111,2-Bis(12-methoxydodecanoyl)-sn-glycero-3-phosphocholine

Product 1

HCID 454704HCID 454704, compound

Procedure

The preparation of D-AC2 was identical to L-AC2 except D-glycerolphosphocholine, which was obtained from Synthetische Phosphor-Lipide, Biochemisches Labor, Bern CH Switzerland was used. L-PE2 was prepared by reacting glycerolphosphatidylethanolamine (L-a-GPE) with N-(9-Fluorenylmethoxycarbonyloxy) succinimide (FMOC-succinimide) to form L-a-GPE-FMOC followed by diacylation with 12MO anhydride then deprotection of FMOC with piperidine. L-PE1 was prepared by diacylating L-a-GPE-FMOC with myristic anhydride, then PLA2 cleavage to remove the sn-2 chain, then acylation with 12MO anhydride, and finally deprotection with piperidine to remove FMOC. ##STR47##

Workup

  1. customto form L-a-GPE-FMOC
  2. customL-PE1 was prepared
  3. customPLA2 cleavage to remove the sn-2 chain
  4. customacylation with 12MO anhydride, and finally deprotection with piperidine to remove FMOC

Sources & evidence

ORD record
ord-7e6850bc84e94e198961b7a505b55449
Source dataset
uspto-grants-1998_12
Patent number
US05846955

Reaction notes

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