HCID 86594389, compound → HCID 86594390, compound

HRID 2428056Notes

Reaction equation

HRID 2428056 reaction equation
[C:1](=[O:61])([O:3][C@@H:4]([C@@H:55]([CH3:60])/[CH:56]=[CH:57]\[CH:58]=[CH2:59])[C@@H:5]([CH3:54])[C@H:6]([O:44]CC1C=CC(OC)=CC=1)[CH2:7][CH2:8]/[CH:9]=[CH:10]\[C@H:11]([CH3:43])[C@H:12]([O:33]CC1C=CC(OC)=CC=1)[C@@H:13]([CH3:32])/[CH:14]=[CH:15]\[CH2:16][CH2:17][C@H:18]1[C@H:23]([CH3:24])[C@H:22]([O:25][CH2:26][O:27][CH3:28])[C@@H:21]([CH3:29])[C@H:20]([O:30][CH3:31])[O:19]1)[NH2:2].C(=O)(O[C@@H]([C@@H](C)/C=C\C=C)[C@@H](C)[C@H](O)CC/C=C\[C@H](C)[C@H](O)[C@@H](C)/C=C\CC[C@H]1[C@@H](C)[C@H](O)[C@@H](C)C(=O)O1)N>CCOC(C)=O.CCCCCC>[C:1](=[O:61])([O:3][C@@H:4]([C@@H:55]([CH3:60])/[CH:56]=[CH:57]\[CH:58]=[CH2:59])[C@@H:5]([CH3:54])[C@H:6]([OH:44])[CH2:7][CH2:8]/[CH:9]=[CH:10]\[C@H:11]([CH3:43])[C@H:12]([OH:33])[C@@H:13]([CH3:32])/[CH:14]=[CH:15]\[CH2:16][CH2:17][C@H:18]1[C@H:23]([CH3:24])[C@H:22]([O:25][CH2:26][O:27][CH3:28])[C@@H:21]([CH3:29])[C@H:20]([O:30][CH3:31])[O:19]1)[NH2:2]

Participants

4

Reactant 2

HCID 86594389HCID 86594389, compoundHCID 131725991HCID 131725991, compound

Product 1

HCID 86594390HCID 86594390, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

Carbamate 39 (4.25 mg, 0.005 mmol) was subjected to the deprotection procedure of PMB described in the preparation of 40. Flash chromatography (EtOAc/hexane 3:2) of the crude product provided 42 (2.8 mg, 92%) as a colorless oil: IR(CHCl3) 3115, 2749, 2328, 1676, 1508, 1215 cm−1; 1H NMR (300 MHz, CDCl3) 6.76 (ddd, 1H, J=16.8, 11.0, 10.1 Hz), 6.18 (t, 1H, J=10.8 Hz), 5.70-5.46 (m, 5H), 5.35 (d, 1H, J=16.8 Hz), 4.49 (dd, J=4.5, 6.6 Hz), 4.82 (d, 2H, J=2.4 Hz), 4.73 (br s, 2H), 4.43 (d, 1H, J=5.1 Hz), 4.15, (m, 1H), 3.78 (m, 1H), 3.56 (s, 3H), 3.54 (s, 3H), 3.36 (t, 2H, J=6.9 Hz), 3.14 (m, 1H), 2.76 (m, 2H), 2.35-2.18 (m, 6H), 2.00-1.60 (m, 7H), 1.22 (d, 3H, J=7.2 Hz), 1.16-1.12 (m, 12H), 1.07 (d, 3H, J=7.2 Hz); 13C NMR (125 MHz, CDCl3) 157.3, 133.7, 133.5, 132.2, 132.0, 130.0, 128.7, 118.0, 109.6, 103.0, 96.5, 82.1, 79.7, 79.1, 72.7, 55.8, 39.9, 39.5, 38.3, 35.5, 35.0, 34.8, 34.6, 30.2, 29.8, 24.3, 18.1, 17.7, 15.7, 15.4, 14.2, 13.2, 8.1; LRMS (ESI) 632.4 (M+Na); HRMS (ESI) calcd for C33H55NO8Na 632.4138, found 632.4139; [α]20D+21.6 (c 0.25, CHCl3).

Sources & evidence

ORD record
ord-73c98db711f448fb9a21a27e890e4887
Source dataset
uspto-grants-2011_06
Patent number
US07968736B2

Reaction notes

Loading…