Methanol → HCID 131730294, compound

HRID 1944838Notes

Reaction equation

HRID 1944838 reaction equation
[NH:1]([C:7]([O:9][CH2:10][CH:11]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17]2[C:12]1=[CH:13][CH:14]=[CH:15][CH:16]=2)=[O:8])[CH2:2][CH2:3][C:4]([OH:6])=[O:5].[NH2:24][CH:25]([CH2:28][OH:29])[CH2:26][OH:27].[C:30](Cl)([C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)([C:39]1[CH:46]=[CH:45][C:42]([O:43][CH3:44])=[CH:41][CH:40]=1)[C:31]1[CH:38]=[CH:37][C:34]([O:35][CH3:36])=[CH:33][CH:32]=1.CO>N1C=CC=CC=1>[NH:1]([C:7]([O:9][CH2:10][CH:11]1[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:18]2[C:23]1=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:8])[CH2:2][CH2:3][C:4]([O:6][C:30]([C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)([C:39]1[CH:46]=[CH:45][C:42]([O:43][CH3:44])=[CH:41][CH:40]=1)[C:31]1[CH:32]=[CH:33][C:34]([O:35][CH3:36])=[CH:37][CH:38]=1)=[O:5].[NH2:24][CH:25]([CH2:28][OH:29])[CH2:26][OH:27]

Participants

5

Reactant 3

HCID 887MethanolHCID 968311,1'-(Chlorophenylmethylene)bis(4-methoxybenzene)HCID 131730293HCID 131730293, compound

Product 1

HCID 131730294HCID 131730294, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

N-Fmoc-β-Ala-Serinol (1, 93 g, 242 mmol) is co-evaporated 2×400 mL anh. pyridine, and then dissolved in 300 mL of the same solvent with magnetic stirring. The mixture is cooled in a ice bath, and DMT-Cl (86.1 g, 254 mmol) in 465 mL pyridine is added dropwise over a period of 1.5 hours. The ice bath is removed and the mixture is allowed to react for another hour at room temperature. Methanol (100 mL) is added and stirred for 15 min. to quench the remaining DMT-Cl. After evaporation in vacuo, the residue co-evaporated 3×400 mL with toluene. Silica gel column purification using ethyl acetate/methanol/triethylamine (95:5:0.25) as mobile phase yielded 90.6 g (55%) grams of isolated product 2.

Workup

  1. temperatureThe mixture is cooled in a ice bath
  2. customThe ice bath is removed
  3. customto react for another hour at room temperature
  4. customto quench the remaining DMT-Cl
  5. customAfter evaporation in vacuo
  6. customSilica gel column purification

Sources & evidence

ORD record
ord-145c41ee0a0b4cbcbe5b97a2dd01943d
Source dataset
uspto-grants-2013_03
Patent number
US08394948B2

Reaction notes

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