2-(Methylamino)ethanol → HCID 58748182, compound

HRID 1162653Notes

Reaction equation

[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:9][C@H:10]2[CH2:14][N:13]([CH2:15][C:16](=[O:32])[NH:17][C:18]3[CH:23]=[CH:22][C:21]([N:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]4=[O:30])=[CH:20][C:19]=3[F:31])[CH2:12][C@@H:11]2[C:33]([O-:35])=O)=[O:8])=[CH:4][CH:3]=1.[Li+].C1N=CN(C(N2C=NC=C2)=O)C=1.[CH3:49][NH:50][CH2:51][CH2:52][OH:53]>C1COCC1.CN(C=O)C>[OH:53][CH2:52][CH2:51][N:50]([CH3:49])[C:33]([C@@H:11]1[C@@H:10]([NH:9][C:7]([C:5]2[S:6][C:2]([Cl:1])=[CH:3][CH:4]=2)=[O:8])[CH2:14][N:13]([CH2:15][C:16](=[O:32])[NH:17][C:18]2[CH:23]=[CH:22][C:21]([N:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]3=[O:30])=[CH:20][C:19]=2[F:31])[CH2:12]1)=[O:35]

Participants

Conditions

Temperature: 25 °C

Procedure

Lithium (3S,4R)-4-[(5-chloro-thiophene-2-carbonyl)-amino]-1-{[2-fluoro-4-(2-oxo-2H-pyridin-1-yl)-phenylcarbamoyl]-methyl}-pyrrolidine-3-carboxylate (example 41; 0.09 g) is dissolved in THF/DMF (1:1; 3 ml) and CDI (0.083 g) is added. The mixture is stirred for 1 h at 25° C., after that 2-(methylamino)-ethanol (0.03 ml) is added. The reaction mixture is stirred for 18 h at 25° C. and evaporated to dryness followed by flash chromatography over silica gel using DCM/MeOH/NH3 as eluent to yield 0.033 g (33.4%) (3S,4R)-4-[(5-chloro-thiophene-2-carbonyl)-amino]-1-{[2-fluoro-4-(2-oxo-2H-pyridin-1-yl)-phenylcarbamoyl]-methyl}-pyrrolidine-3-carboxylic acid (2-hydroxy-ethyl)-methyl-amide. White solid. MS 576.5 [M+H+].

Workup

stirringThe reaction mixture is stirred for 18 h at 25° C.
customevaporated to dryness

Sources & evidence

ORD record: ord-07b48efeabcc4b59ad0b23e4e0781d7b
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07820699B2

Reaction notes

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