Hydrochloric Acid → HCID 19695839, compound

HRID 375604Notes

Reaction equation

HRID 375604 reaction equation
[F:1][C:2]([F:49])([C:38](=[O:48])[NH:39][CH2:40][CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[CH:3]([OH:37])[CH:4]([NH:8][C:9](=[O:36])[CH2:10][N:11]1[C:16]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:15][CH:14]=[C:13]([NH:23][C:24]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([CH3:34])[N:29]=2)=[O:25])[C:12]1=[O:35])[CH:5]([CH3:7])[CH3:6].Cl>>[F:49][C:2]([F:1])([C:38](=[O:48])[NH:39][CH2:40][CH2:41][C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1)[C:3](=[O:37])[CH:4]([NH:8][C:9](=[O:36])[CH2:10][N:11]1[C:16]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[CH:15][CH:14]=[C:13]([NH:23][C:24]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([CH3:34])[N:29]=2)=[O:25])[C:12]1=[O:35])[CH:5]([CH3:6])[CH3:7]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 19695820N-[3,3-Difluoro-2-hydroxy-1-isopropyl-3-(N-phenethylcarbamoyl)propyl]-2-[3-(6-methylpyrid-2-ylmethoxycarbonylamino)-2-oxo-6-phenyl-1,2-dihydro-1-pyridyl]acetamide

Product 1

HCID 19695839HCID 19695839, compound

Procedure

N-[3,3-Difluoro-2-hydroxy-1-isopropyl-3-(N-phenethylcarbamoyl)propyl]-2-[3-(6-methylpyrid-2-ylmethoxycarbonylamino)-2-oxo-6-phenyl-1,2-dihydro-1-pyridyl]acetamide was oxidized using a procedure similar to that described in Example 1.i., but omitting the hydrochloric acid wash. The crude material was purified by chromatography, with methanol:chloroform (1:99) as the eluent. The resulting material was triturated with diethyl ether and petroleum ether to give a solid which was triturated with petroleum ether to yield the title compound; TLC: Rf =0.31, chloroform:methanol (30:1); 300 MHz NMR: 9.20 (t,1), 8.68 (s,1), 8.50 (d,1), 7.91 (d,1), 7.71 (t,1), 7.48-7.11 (m,14), 6.22 (d,1), 5.18 (s,2), 4.83-4.75 (m,1), 4.50 (broad s,2), 2.76 (t,2), 2.27-2.12 (m,1), 8.48 (d,3), 7.36 (d,3); MS: m/z=674(M+ 1). Analysis for C37H37F2N5O6 : Calculated: C, 64.18; H, 5.54; N, 10.40; Found: C, 64.21; H, 5.72; N, 10.10.

Workup

  1. washwash
  2. customThe crude material was purified by chromatography, with methanol:chloroform (1:99) as the eluent
  3. customThe resulting material was triturated with diethyl ether and petroleum ether
  4. customto give a solid which
  5. customwas triturated with petroleum ether

Sources & evidence

ORD record
ord-ea9b48b395e94d42bcd02e4ce922cc55
Source dataset
uspto-grants-1996_01
Patent number
US05486529

Reaction notes

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