Piperidine → HCID 86718404, compound

HRID 1755205Notes

Reaction equation

HRID 1755205 reaction equation
[N:1]1([C:7]([O:9][C@H:10](/[CH:12]=[CH:13]\[C:14]([NH:16][C@@H:17]2[CH2:22][C@H:21]([CH3:23])[C@H:20]([CH2:24]/[CH:25]=[C:26](\[CH3:49])/[CH:27]=[CH:28]/[C@H:29]3[O:36][C@H:35]([CH2:37][C:38]([NH2:40])=[O:39])[CH2:34][C@:31]4([O:33][CH2:32]4)[C@@H:30]3[O:41][Si](C(C)(C)C)(C)C)[O:19][C@@H:18]2[CH3:50])=[O:15])[CH3:11])=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[N+](C1C=CC(OC(=O)OC2C=CC([N+]([O-])=O)=CC=2)=CC=1)([O-])=O.N1CCCCC1.CN(CCSC)C(=O)O[C@H](/C=C\C(N[C@@H]1C[C@H](C)[C@H](C/C=C(\C)/C=C/[C@H]2O[C@H](CC(N)=O)C[C@]3(OC3)[C@@H]2O[Si](C(C)(C)C)(C)C)O[C@@H]1C)=O)C>>[N:1]1([C:7]([O:9][C@H:10](/[CH:12]=[CH:13]\[C:14]([NH:16][C@@H:17]2[CH2:22][C@H:21]([CH3:23])[C@H:20]([CH2:24]/[CH:25]=[C:26](\[CH3:49])/[CH:27]=[CH:28]/[C@H:29]3[O:36][C@H:35]([CH2:37][C:38]([NH2:40])=[O:39])[CH2:34][C@:31]4([O:33][CH2:32]4)[C@@H:30]3[OH:41])[O:19][C@@H:18]2[CH3:50])=[O:15])[CH3:11])=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 5

HCID 8082PiperidineHCID 8471TriethylamineHCID 78756Bis(4-nitrophenyl) carbonateHCID 86718405HCID 86718405, compoundHCID 86718406HCID 86718406, compound

Product 1

HCID 86718404HCID 86718404, compoundYield 18%

Procedure

Synthesis of (2S,3Z)-5-{[(2R,3R,5S,6S)-6-{(2E,4E)-5-[(3R,4R,5R,7S)-7-(2- amino-2-oxoethyl)-4-{[tert-butyl(dimethyl)silyl]oxy}-1,6-dioxaspiro[2.5]oct-5-yl]-3-methylpenta-2,4-dien-1-yl}-2,5-dimethyltetrahydro-2H-pyran-3-yl]amino}-5-oxopent-3-en-2-yl piperidine-1-carboxylate (#B135). Using the procedure described in step 3 of example A42, the title compound was prepared in 18% yield from 63.2 mg (0.104 mmol, 1.0 eq) of #B132, triethylamine (73 μL, 0.520 mmol, 5 eq), 4-N,N-dimethylamino pyridine (8.9 mg, 0.073 mmol, 0.7 eq.) and bis-(4-nitrophenyl)-carbonate (106 mg, 0.343 mmol, 3.3 eq.) and piperidine (14.8 mg, 0.174 mmol, 1.7 eq.) using the procedure described for preparation of compound #B133. LCMS (Protocol D): m/z 740.5 [M+Na]+, retention time=1.13 minutes.

Sources & evidence

ORD record
ord-64be5b549599437ca6daf8eb475eab62
Source dataset
uspto-grants-2015_10
Patent number
US09169264B2

Reaction notes

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