Acetic Anhydride → HCID 86727209, compound

HRID 2274318Notes

Reaction equation

HRID 2274318 reaction equation
[C:1]([O:4][C:5](=[O:7])[CH3:6])(=O)[CH3:2].[CH2:8]([O:15][C@@H:16]1[C@H:21]2[NH:22][C:23](=[O:25])[O:24][C@H:20]2[CH2:19][C@H:18](C(O)C)[C@H:17]1[O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>N1C=CC=CC=1>[C:5]([O:4][CH:1]([C@@H:18]1[C@@H:17]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C@H:16]([O:15][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C@H:21]2[NH:22][C:23](=[O:25])[O:24][C@H:20]2[CH2:19]1)[CH3:2])(=[O:7])[CH3:6]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 86727208HCID 86727208, compound

Product 1

HCID 86727209HCID 86727209, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Acetic anhydride (3.3 g, 32 mmol) was added to a solution of 4 (1.0 g, 2.5 mmol) in pyridine (60 mL) and the solution was stirred overnight at room temperature. The mixture was concentrated in vacuo to give a residue, which was purified by a silica gel column, eluted with 2% MeOH in DCM to give 5 as yellow oil (900 mg, 81%, the ratio of diastereomers is 1:3 by 1H NMR). (ES, m/z): [M+H]+ 457.1; 1H NMR (300 MHz, CDCl3) δ 7.32-7.43 (m, 10H), 4.91-4.95 (m, 1H), 4.72-4.78 (m, 3H), 4.56-4.66 (m, 2H), 4.47-4.50 (m, 1H), 3.61-3.63 (m, 1H), 3.49-3.54 (m, 1H), 3.32-3.35 (m, 1H), 2.03 (s, 3H), 1.51-1.76 (m, 2H), 1.27 (d, J=6.3 Hz, 3H).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customto give a residue, which
  3. customwas purified by a silica gel column
  4. washeluted with 2% MeOH in DCM

Sources & evidence

ORD record
ord-3b34ad53dc03499b9d0dcb33e50d04e2
Source dataset
uspto-grants-2015_09
Patent number
US09126957B2

Reaction notes

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