Thionyl Chloride → HCID 54337571, compound

HRID 262912Notes

Reaction equation

HRID 262912 reaction equation
[C:1]([NH:11][C@H:12]([C:20]([OH:22])=O)[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].S(Cl)(Cl)=O.Cl.[CH3:28][N:29]1[C:37]2[C:32](=[CH:33][C:34]([Cl:38])=[CH:35][CH:36]=2)[C:31]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=2[Cl:45])=[C:30]1[CH2:46][NH2:47].C(=O)(O)[O-].[Na+]>CN(C)P(=O)(N(C)C)N(C)C.CCOCC.C(N(CC)CC)C>[CH3:28][N:29]1[C:37]2[C:32](=[CH:33][C:34]([Cl:38])=[CH:35][CH:36]=2)[C:31]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=2[Cl:45])=[C:30]1[CH2:46][NH:47][C:20](=[O:22])[C@H:12]([CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[NH:11][C:1]([O:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:2]

Participants

8

Reactant 4

HCID 24386Thionyl ChlorideHCID 70878Benzyloxycarbonyl-L-phenylalanineHCID 516892Sodium BicarbonateHCID 70582520HCID 70582520, compound

Product 1

HCID 54337571HCID 54337571, compoundYield 53.6%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolvent2×HCID 8471TriethylamineSolventHCID 12679HexamethylphosphoramideSolvent

Procedure

To a solution of N-carbobenzoxy-phenylalanine (3 g) in hexamethylphosphoric triamide (16 ml), thionyl chloride (1.2 g) is added dropwise at -6° to -2° C. in 5 minutes, and the resultant mixture is stirred at -6° to -8° C. for 10 minutes. To the mixture, a suspension of 1-methyl-2-aminomethyl-3-o-chlorophenyl-5-chloroindole hydrochloride (3.52 g) in ether (15 ml) previously treated with triethylamine is added, and the resultant mixture is allowed to stand at room temperature overnight. The reaction mixture is neutralized with an aqueous sodium bicarbonate solution and shaken with ether. The organic layer is dried and evaporated to remove the ether. The residue is crystallized from ether to give 1-methyl-2-(Nα -carbobenzoxy-phenylalanylaminomethyl)-3-o-chlorophenyl-5-chloroindole (3.15 g). This substance is recrystallized from ethyl acetate to give needles melting at 174° to 176° C. The yield is 54%. UV: λmaxEtOH 232, 285 mμ (log ε=4.88, 3.28).

Workup

  1. additionis added
  2. customThe organic layer is dried
  3. customevaporated
  4. customto remove the ether
  5. customThe residue is crystallized from ether

Sources & evidence

ORD record
ord-1ef4e77ed6be49e6b3e7c2fbb80ffe29
Source dataset
uspto-grants-1979_05
Patent number
US04154727

Reaction notes

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