Methanol → HCID 131736689, compound

HRID 1482244Notes

Reaction equation

HRID 1482244 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([C:7]([Cl:21])([C:14]2[C:19]([Cl:20])=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:3][CH:2]=1.CO.C(N(C(C)C)CC)(C)C.[CH:33]1[C:45]2[CH:44]([CH2:46][O:47][C:48]([NH:50][C@H:51]([C:66](=[O:73])[N:67]3[CH2:72][CH2:71][CH2:70][CH2:69][CH2:68]3)[CH2:52][C:53]3[CH:54]=[C:55]([C:59](=[CH2:65])[CH2:60][CH2:61][C:62]([OH:64])=[O:63])[CH:56]=[CH:57][CH:58]=3)=[O:49])[C:43]3[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=3)[C:37]=2[CH:36]=[CH:35][CH:34]=1>ClCCl>[CH:42]1[C:43]2[CH:44]([CH2:46][O:47][C:48]([NH:50][C@H:51]([C:66](=[O:73])[N:67]3[CH2:72][CH2:71][CH2:70][CH2:69][CH2:68]3)[CH2:52][C:53]3[CH:54]=[C:55]([C:59](=[CH2:65])[CH2:60][CH2:61][C:62]([OH:64])=[O:63])[CH:56]=[CH:57][CH:58]=3)=[O:49])[C:45]3[C:37](=[CH:36][CH:35]=[CH:34][CH:33]=3)[C:38]=2[CH:39]=[CH:40][CH:41]=1.[CH:11]1[CH:10]=[CH:9][C:8]([C:7]([Cl:21])([C:14]2[C:19]([Cl:20])=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:4]2[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=2)=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 81531DiisopropylethylamineHCID 945242-Chlorotrityl chlorideHCID 89668329HCID 89668329, compound

Product 1

HCID 131736689HCID 131736689, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2-Chlorotrityl chloride resin (1.07 mmol/g, 100-200 mesh, 1% DVB, manufactured by Chem-Impex, 2.50 g, 2.68 mmol) and dichloromethane (18 ml) were mixed, followed by shaking at room temperature for 5 minutes. Dichloromethane was removed, after which methanol (0.43 ml, 10.7 mmol) and diisopropylethylamine (1.1 ml, 6.32 mmol) were added to a solution of (S)-4-(3-(2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-oxo-3-(piperidin-1-yl)propyl)phenyl)pent-4-enoic acid (Compound SP421) (0.74 g, 1.34 mmol) in dichloromethane (16.5 ml) and the resulting mixture was added to the resin, followed by shaking at room temperature for 10 minutes. The reaction solution was removed, after which methanol (5 ml) and diisopropylethylamine (1.7 ml) were added to dichloromethane (16.5 ml), and the resulting mixture was added, followed by shaking at room temperature for 2 hours. This reaction solution was removed, and dichloromethane (18 ml) was then placed, followed by shaking. Dichloromethane was removed, and dichloromethane (18 ml) was then placed again, followed by shaking. Dichloromethane was removed, and the resin was then dried under reduced pressure to afford the title compound SP422 (2.52 g).

Workup

  1. customDichloromethane was removed
  2. additionthe resulting mixture was added to the resin
  3. stirringby shaking at room temperature for 10 minutes
  4. customThe reaction solution was removed
  5. additionafter which methanol (5 ml) and diisopropylethylamine (1.7 ml) were added to dichloromethane (16.5 ml)
  6. additionthe resulting mixture was added
  7. stirringby shaking at room temperature for 2 hours
  8. customThis reaction solution was removed
  9. stirringby shaking
  10. customDichloromethane was removed
  11. stirringby shaking
  12. customDichloromethane was removed
  13. customthe resin was then dried under reduced pressure

Sources & evidence

ORD record
ord-bef268152aaf4bb095a4d7cbb35775c6
Source dataset
uspto-grants-2016_08
Patent number
US09409952B2

Reaction notes

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