Ammonia → HCID 86625133, compound

HRID 1929546Notes

Reaction equation

HRID 1929546 reaction equation
C[O:2][C:3](=O)[C@@H:4]1[CH2:8][CH2:7][CH2:6][N:5]1[CH2:9][C:10]1[C:11]2[C:16]([C:17]3[CH:18]=[C:19]4[O:26][CH2:25][O:24][C:20]4=[CH:21][C:22]=3[CH:23]=1)=[CH:15][C:14]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[CH:13][CH:12]=2.N>>[CH2:25]1[O:26][C:19]2[C:20](=[CH:21][C:22]3[CH:23]=[C:10]([CH2:9][N:5]4[CH2:6][CH2:7][CH2:8][C@H:4]4[CH2:3][OH:2])[C:11]4[C:16]([C:17]=3[CH:18]=2)=[CH:15][C:14]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:13][CH:12]=4)[O:24]1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 24205685HCID 24205685, compound

Product 1

HCID 86625133HCID 86625133, compound

Procedure

General procedure f from 17 (95%); colorless oil, recrystallization from EtOH gave white powder; mp 122-124° C.; 1H NMR (400.13 MHz) δ 8.13 (d, J=4 Hz, 1H), 7.90 (d, J=2 Hz, 1H), 7.84 (s, 1H), 7.51 (d, J=4 Hz, 2H), 7.42 (s, 1H), 7.41 (t, J=4 Hz, 2H), 7.34 (m, 1H), 7.29 (dd, J=4 Hz, 2 Hz, 1H), 7.14 (s, 1H), 6.06 (s, 2H), 5.24 (s, 2H), 4.36 (d, J=7 Hz, 2H), 3.78 (d, J=17 Hz, 2H), 3.41 (m, 1H), 2.42 (m, 2H), 1.83 (m, 2H), 1.66 (m, 6H); MS (DCI/NH3) m/e: 442 (M+H)+. Anal. (C28H27O4N) C, H, N.

Workup

  1. customcolorless oil, recrystallization from EtOH
  2. customgave white powder

Sources & evidence

ORD record
ord-a5b90cf9ba9449e0851621d4bd61ecf8
Source dataset
uspto-grants-2012_05
Patent number
US08188089B2

Reaction notes

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