HCID 67588604, compound → HCID 53806265, compound

HRID 1416789Notes

Reaction equation

HRID 1416789 reaction equation
[C:1]1([CH:7]=[CH:8][CH2:9][O:10][C:11]([C:13]2([C:44]([O:46][CH2:47][CH:48]=[CH:49][C:50]3[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=3)=[O:45])[O:17][C:16]3[CH:18]=[CH:19][C:20]([CH2:22][C@H:23]([N:25]([CH2:34][C@@H:35]([C:37]4[CH:42]=[CH:41][CH:40]=[C:39]([Cl:43])[CH:38]=4)[OH:36])C(OCC(Cl)(Cl)Cl)=O)[CH3:24])=[CH:21][C:15]=3[O:14]2)=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C(Cl)(Cl)Cl.CO>[C:1]1([CH:7]=[CH:8][CH2:9][O:10][C:11]([C:13]2([C:44]([O:46][CH2:47][CH:48]=[CH:49][C:50]3[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=3)=[O:45])[O:17][C:16]3[CH:18]=[CH:19][C:20]([CH2:22][C@H:23]([NH:25][CH2:34][C@@H:35]([C:37]4[CH:42]=[CH:41][CH:40]=[C:39]([Cl:43])[CH:38]=4)[OH:36])[CH3:24])=[CH:21][C:15]=3[O:14]2)=[O:12])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

3

Reactant 1

HCID 67588604HCID 67588604, compound

Product 1

HCID 53806265HCID 53806265, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

The fide compound was prepared as a colorless oil according to the procedure of Example 4, Step 6 except that 5-{(2R)-2-[[(2R)2-(3-chloro-phenyl)-2-hydroxy-ethyl]-(2,2,2-trichloro-ethoxycarbonyl)-amino]-propyl}-benzo[1,3]dioxole-2,2-dicarboxylic acid bis-(3-phenyl-allyl) ester was used in place of 5-{(2R)-2-[[(2R)-2-(3-chloro-phenyl)-2-hydroxy-ethyl]-(2,2,2-trichloro-ethoxycarbonyl)-amino]-propyl}-benzo[1,3]dioxole-2,2-dicarboxylic acid diallyl ester; yield 59%; Rf =0.35 (10/1 CHCl3 /MeOH); 1H NMR (300 MHz, CDCl3): δ 1.15 (d, J=6.3 Hz, 3H), 2.50-3.70 (brs, 2H), 2.60-2.71 (m, 1H), 2.80-2.92 (m, 2H), 2.95-3.15 (m, 2H), 4.83-4.95 (m, 5H), 5.25-5.40 (m, 4H), 6.08-6.30 (complex m, 2H), 6.66-6.91 (m, 5H), 7.15-7.40 (m, 14H); MS (ES) m/z (relative intensity): 654 (M+, 100).

Workup

  1. customThe fide compound was prepared as a colorless oil

Sources & evidence

ORD record
ord-24c4320356f74127a4d0ffdc97b1dccb
Source dataset
uspto-grants-1999_06
Patent number
US05914339

Reaction notes

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