Methanol → HCID 136404630, compound

HRID 613348Notes

Reaction equation

HRID 613348 reaction equation
[BH4-].[Na+].C(Cl)Cl.CO.[CH:8]([C:10]1[CH:14]=[C:13]2[C:15]([C:73]3[CH:78]=[CH:77][CH:76]=[CH:75][C:74]=3[NH:79][C:80](=[O:85])[C:81]([CH3:84])([CH3:83])[CH3:82])=[C:16]3[N:20]=[C:19]([C:21]([C:60]4[CH:65]=[CH:64][CH:63]=[CH:62][C:61]=4[NH:66][C:67](=[O:72])[C:68]([CH3:71])([CH3:70])[CH3:69])=[C:22]4[NH:26][C:25](=[C:27]([C:47]5[CH:52]=[CH:51][CH:50]=[CH:49][C:48]=5[NH:53][C:54](=[O:59])[C:55]([CH3:58])([CH3:57])[CH3:56])[C:28]5[CH:29]=[CH:30][C:31](=[C:33]([C:34]6[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=6[NH:40][C:41](=[O:46])[C:42]([CH3:45])([CH3:44])[CH3:43])[C:11]=1[NH:12]2)[N:32]=5)[CH:24]=[CH:23]4)[CH:18]=[CH:17]3)=[O:9]>O>[OH:9][CH2:8][C:10]1[CH:14]=[C:13]2[C:15]([C:73]3[CH:78]=[CH:77][CH:76]=[CH:75][C:74]=3[NH:79][C:80](=[O:85])[C:81]([CH3:84])([CH3:83])[CH3:82])=[C:16]3[N:20]=[C:19]([C:21]([C:60]4[CH:65]=[CH:64][CH:63]=[CH:62][C:61]=4[NH:66][C:67](=[O:72])[C:68]([CH3:69])([CH3:70])[CH3:71])=[C:22]4[NH:26][C:25](=[C:27]([C:47]5[CH:52]=[CH:51][CH:50]=[CH:49][C:48]=5[NH:53][C:54](=[O:59])[C:55]([CH3:56])([CH3:57])[CH3:58])[C:28]5[CH:29]=[CH:30][C:31](=[C:33]([C:34]6[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=6[NH:40][C:41](=[O:46])[C:42]([CH3:43])([CH3:44])[CH3:45])[C:11]=1[NH:12]2)[N:32]=5)[CH:24]=[CH:23]4)[CH:18]=[CH:17]3

Participants

6

Reactant 4

HCID 887MethanolHCID 6344DichloromethaneHCID 4311764Sodium borohydrideHCID 16167393HCID 16167393, compound

Product 1

HCID 136404630HCID 136404630, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

NaBH4 (41.5 mg, 1.1 mmol) was added to a solution of CH2Cl2 --MeOH (1/3 v/v) (8 ml) containing 2-formyl-5,10,15,20-tetrakis(o-pivalamidophenyl)porphyrin (0.11 g, 0.11 mmol) under argon stirred for 15 min. After adding water to the solution, the mixture was extracted by CHCl3 and washed with water. After drying (Na2SO4), the organic layer was chromatographed on a silica gel flash column using CHCl3 --MeOH (10/1 v/v) as the eluent. The residue was dried at room temperature in vacuo to give a purple product, (2-hydroxymethyl-5,10,15,20-tetrakis(o-pivalamidophenyl)porphyrin, 0.11 g, 94%).

Workup

  1. extractionthe mixture was extracted by CHCl3
  2. washwashed with water
  3. dry with materialAfter drying (Na2SO4)
  4. customthe organic layer was chromatographed on a silica gel flash column
  5. customThe residue was dried at room temperature in vacuo

Sources & evidence

ORD record
ord-f438c2ec0f2d427da719100d28780c8b
Source dataset
uspto-grants-1999_12
Patent number
US06008198

Reaction notes

Loading…