Triethylamine → HCID 86760601, compound

HRID 2252509Notes

Reaction equation

HRID 2252509 reaction equation
C[O:2][C:3](=[O:68])/[CH:4]=[CH:5]\[CH:6]=[CH:7]\[C@H:8]([CH3:67])[C@@H:9]([O:59][Si:60]([C:63]([CH3:66])([CH3:65])[CH3:64])([CH3:62])[CH3:61])[CH2:10][C@H:11]([O:51][Si:52]([C:55]([CH3:58])([CH3:57])[CH3:56])([CH3:54])[CH3:53])/[CH:12]=[CH:13]\[C@H:14]([CH3:50])[C@H:15]([O:42][Si:43]([C:46]([CH3:49])([CH3:48])[CH3:47])([CH3:45])[CH3:44])[C@H:16]([CH3:41])[CH2:17][C@@H:18]([CH3:40])[CH2:19][CH2:20][C@H:21]([O:32][Si:33]([C:36]([CH3:39])([CH3:38])[CH3:37])([CH3:35])[CH3:34])[C@H:22]([CH3:31])[C@@H:23]([OH:30])[C@@H:24]([CH3:29])/[CH:25]=[CH:26]\[CH:27]=[CH2:28].[OH-].[K+].ClC1C=C(Cl)C=C(Cl)C=1C(Cl)=O.CCN(CC)CC>CN(C1C=CN=CC=1)C.C(Cl)(Cl)Cl.CCOC(C)=O.CCCCCC>[Si:60]([O:59][C@@H:9]([CH2:10][C@H:11]([O:51][Si:52]([C:55]([CH3:58])([CH3:57])[CH3:56])([CH3:53])[CH3:54])/[CH:12]=[CH:13]\[C@H:14]([CH3:50])[C@H:15]([O:42][Si:43]([C:46]([CH3:49])([CH3:48])[CH3:47])([CH3:44])[CH3:45])[C@H:16]([CH3:41])[CH2:17][C@@H:18]([CH3:40])[CH2:19][CH2:20][C@H:21]([O:32][Si:33]([C:36]([CH3:37])([CH3:38])[CH3:39])([CH3:35])[CH3:34])[C@H:22]([CH3:31])[C@@H:23]([OH:30])[C@@H:24]([CH3:29])/[CH:25]=[CH:26]\[CH:27]=[CH2:28])[C@@H:8]([CH3:67])/[CH:7]=[CH:6]/[CH:5]=[CH:4]\[C:3]([OH:68])=[O:2])([C:63]([CH3:64])([CH3:65])[CH3:66])([CH3:62])[CH3:61]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 14797Potassium HydroxideHCID 27337032,4,6-Trichlorobenzoyl chlorideHCID 86760602HCID 86760602, compound

Product 1

HCID 86760601HCID 86760601, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6212ChloroformSolvent2×HCID 21226206Ethyl acetate hexaneSolvent

Procedure

The procedure for 99 was used with 106 (0.13 g, 0.13 μmol) and 1N KOH (1.2 mL, 1.3 mmol), 2,4,6-trichlorobenzoyl chloride (0.094 mL, 0.60 μmol) and Et3N (0.10 mL, 0.78 mmol), 4-DMAP (60 mL, 1.3 mmol) to yield 0.054 g (45% for 2 steps) of the product by flash column chromatography (EtOAc/hexane 1:19) as a colorless oil: (seco acid) IR (CHCl3) 2956, 2857, 1692, 1634, 1471, 1462, 1254, 1076, 836, 773 cm−1; 1H NMR (300 MHz, CDCl3) δ 7.34 (dd, J=15.2, 11.3 Hz, 1H), 6.66 (ddd, J=16.8, 10.8, 10.6 Hz, 1H), 6.62 (t, J=11.3 Hz, 1H), 6.23 (dd, J=15.3, 6.0 Hz, 1H), 6.09 (t, J=11.0 Hz, 1H), 5.57 (d, J=11.2 Hz, 1H), 5.48-5.42 (m, 1H), 5.35-5.28 (m, 1H), 5.20 (d, J=16.8 Hz, 1H), 5.10 (d, J=10.2 Hz, 1H), 4.55 (m, 1H), 3.95 (m, 1H), 3.74 (m, 1H), 3.26 (m, 1H), 2.78 (m, 1H), 2.58 (m, 2H), 1.75-1.64 (m, 2H), 1.62-1.49 (m, 3H), 1.44-1.37 (m, 1H), 1.32-1.19 (m, 3H), 1.04 (d, J=7.0 Hz, 3H), 1.01 (d, J=7.0 Hz, 3H), 1.00 (d, J=6.4 Hz, 3H), 0.95-0.86 (m, 41H), 0.82 (d, J=7.1 Hz, 3H), 0.81 (d, J=6.4 Hz, 3H), 0.12-0.05 (m, 24H); 13C NMR (75 MHz, CDCl3) δ 171.5, 148.3, 147.4, 136.4, 133.1, 132.6, 131.5, 129.5, 126.6, 117.3, 115.0, 81.3, 78.6, 74.3, 72.7, 66.4, 43.0, 42.7, 39.7, 36.2, 35.8, 35.5, 35.3, 34.1, 32.4, 30.6, 26.3, 26.0, 25.94, 25.92, 19.6, 19.2, 18.5, 18.1, 18.0, 17.4, 16.7, 14.5, 11.0, −2.8, −3.4, −3.5, −4.1, −4.25, −4.32, −4.7; LRMS (ESI) 1029.7 [M+Na]+, 915.8; HRMS (ESI) calcd for C56H110O7Si4Na 1029.7226 [M+Na]+, found 1029.7252; [α]20D−32.7 (c 0.51, CHCl3).

Sources & evidence

ORD record
ord-bb65d68406f14416bac7253773fb8bc9
Source dataset
uspto-grants-2008_01
Patent number
US07321046B2

Reaction notes

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