Pyridine → HCID 131732201, compound

HRID 1408309Notes

Reaction equation

[CH2:1]([NH:7][CH2:8][C@@H:9]([OH:26])[C@@H:10]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:2][CH2:3][CH2:4][CH:5]=[CH2:6].[CH2:27]([O:33][C:34]1[CH:39]=[C:38]([O:40][CH3:41])[CH:37]=[CH:36][C:35]=1[S:42](Cl)(=[O:44])=[O:43])[CH2:28][CH2:29][CH2:30][CH:31]=[CH2:32].N1C=CC=C[CH:47]=1>>[C:21]([O:20][C:19](=[O:25])[NH:18][C@H:10]([C@H:9]([OH:26])[CH2:8][N:7]([CH2:1][CH2:2][CH2:3][CH2:4][CH:5]=[CH2:6])[S:42]([C:35]1[CH:36]=[CH:37][C:38]([O:40][CH2:41][CH3:47])=[CH:39][C:34]=1[O:33][CH2:27][CH2:28][CH2:29][CH2:30][CH:31]=[CH2:32])(=[O:44])=[O:43])[CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)([CH3:22])([CH3:24])[CH3:23]

Participants

Reactant 3

HCID 1049Pyridine

HCID 44598114HCID 44598114, compound

HCID 44598118HCID 44598118, compound

Product 1

HCID 131732201HCID 131732201, compoundYield 84%

Conditions

Temperature: 23 °C

Procedure

To a stirring solution of 10a (50 mg, 0.14 mmol) in pyridine (2 mL) was added 7a (64 mg, 0.20 mmol) and the resulting solution was allowed to stir for 2 h at 23° C. The reaction mixture was concentrated under reduced pressure and the resulting residue was purified by flash column chromatography (3:1 hexanes:EtOAc) to yield 74 mg (84% yield) of 11a as a colorless oil. [α]D20 −1.4 (c 1.00, CHCl3); 1H NMR (400 MHz, CDCl3): δ 1.25-1.34 (m, 12H), 1.47-1.50 (m, 2H), 1.57-1.60 (m, 2H), 1.82-1.90 (m, 2H), 1.97 (q, J=7.1 Hz, 2H), 2.11 (q, J=7.0 Hz, 2H), 2.92-2.95 (m, 2H), 3.10-3.17 (m, 1H), 3.30 (br s, 3H), 3.76 (br s, 2H), 3.84 (s, 3H), 3.90-3.92 (m, 1H) 4.03 (t, J=6.7 Hz, 2H), 4.65 (d, J=7.1 Hz, 1H), 4.89-5.04 (m, 4H), 5.66-5.82 (m, 2H), 6.46 (d, J=2 Hz), 6.49 (dd, J=8.8, 2.3 Hz, 1H), 7.17-7.29 (m, 5H), 7.83 (d, J=7.8 Hz, 1H); 13C NMR (100 MHz, CDCl3): δ 24.9, 25.7, 27.9, 28.2, 28.3, 33.1, 33.2, 35.1, 49.9, 52.3, 54.5, 55.6, 69.1, 72.2, 79.4, 100.2, 104.1, 114.7, 115.0, 119.4, 126.2, 128.3, 129.5, 133.5, 137.8, 138.1, 138.2, 156.0, 157.6, 164.7; FT-IR (film, NaCl) νmax=3395, 2935, 1705, 1597, 1325 cm−1; ESI (+) LRMS m/z (ion): 653.13 (M+Na)+.

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
customthe resulting residue was purified by flash column chromatography (3:1 hexanes:EtOAc)

Sources & evidence

ORD record: ord-e6d58e3baff54a0f9caaa3fcd90de7d8
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08921349B2

Reaction notes

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