Dimethylformamide → HCID 69892327, compound

HRID 1841699Notes

Reaction equation

HRID 1841699 reaction equation
[C:1]([O:5][C:6](NC1C=C(C(O)=O)N(C)C=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:18]([O:27][C:28](=[O:37])[C:29]1[CH:34]=[CH:33][C:32]([CH2:35]Br)=[CH:31][CH:30]=1)[C:19]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:20].C([N:41]([CH:44]([CH3:46])C)[CH2:42][CH3:43])(C)C.CN(C=[O:51])C>>[CH2:18]([O:27][C:28](=[O:37])[C:29]1[CH:34]=[CH:33][C:32]([CH2:35][O:51][C:44]2[NH:41][CH:42]=[CH:43][CH:46]=2)=[CH:31][C:30]=1[C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C:19]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:20]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 27356364-[(tert-Butoxycarbonyl)amino]-1-methyl-1H-pyrrole-2-carboxylic acidHCID 541935972-Oxo-2-phenylethyl 4-(bromomethyl)benzoate

Product 1

HCID 69892327HCID 69892327, compoundYield 97%

Procedure

A solution of Boc-pyrrole-OH (8) (2.9 g 12 mmol), 4-(bromomethyl)benzoic acid phenacyl ester (22) (4 g, 12 mmol) and diisopropylethylamine (3.0 ml, 16.8 mmol) in 60 ml of DMF were stirred at 50° C. for 6 hours. The solution was cooled and partitioned between 400 ml of water and 400 ml of ethyl ether. The ether layer was washed with (2×200 ml each) of 10% citric acid, brine, saturated sodium bicarbonate and brine. The organic phase was dried with sodium sulfate and concentrated in vacuo to yield compound 38 as light white foam which was used without further purification (5.4 g, 97% yield). TLC (2:3 hexane/ethyl acetate) Rf 0.6; 1H NMR (DMSO-d6) δ 9.14 (s, 1H), 8.03 (m, 4H), 7.67 (m, 1H), 7.5 (m, 4H), 7.13 (s, 1H), 6.72 (d, 1H, J=1.5 Hz), 5.74 (s, 1H), 5.32 (s, 1H), 3.79 (s, 3H), 1.42 (s, 9H); 13C NMR (DMSO-d6) δ 193.2, 165.5, 160.4, 153.2, 143.1, 134.5, 130.1, 129.5, 128.3, 128.2, 123.8, 120.3, 118.8, 108.2, 79.1, 67.7, 64.6, 36.7, 28.6.

Workup

  1. temperatureThe solution was cooled
  2. custompartitioned between 400 ml of water and 400 ml of ethyl ether
  3. washThe ether layer was washed with (2×200 ml each) of 10% citric acid, brine, saturated sodium bicarbonate and brine
  4. dry with materialThe organic phase was dried with sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-87680d05c05941cc827ecc399822aea6
Source dataset
uspto-grants-2004_01
Patent number
US06683189B1

Reaction notes

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