Dimethylformamide → tert-butyl N-[[5-[[(2R)-2-[(2R)-4-(4-acetamidophenyl)-3-oxomorpholin-2-yl]-2-hydroxyacetyl]amino]-2-cyanophenyl]methyl]-N-[(2-methylpropan-2-yl)oxycarbonyl]carbamate

HRID 876578Notes

Reaction equation

HRID 876578 reaction equation
[C:1]([NH:4][C:5]1[CH:47]=[CH:46][C:8]([N:9]([C:13](=[O:45])[C@H:14]([OH:44])[C@@H:15]([OH:43])[C:16]([NH:18][C:19]2[CH:20]=[CH:21][C:22]([C:41]#[N:42])=[C:23]([CH2:25][N:26]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[CH:24]=2)=[O:17])[CH2:10][CH2:11]Cl)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].CN(C=O)C>CC(O)(C)C.CS(C)=O>[C:1]([NH:4][C:5]1[CH:47]=[CH:46][C:8]([N:9]2[CH2:10][CH2:11][O:44][C@H:14]([C@@H:15]([OH:43])[C:16]([NH:18][C:19]3[CH:20]=[CH:21][C:22]([C:41]#[N:42])=[C:23]([CH2:25][N:26]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[CH:24]=3)=[O:17])[C:13]2=[O:45])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 6228DimethylformamideHCID 67222317tert-butyl N-[[5-[[(2R,3R)-4-[4-acetamido-N-(2-chloroethyl)anilino]-2,3-dihydroxy-4-oxobutanoyl]amino]-2-cyanophenyl]methyl]-N-[(2-methylpropan-2-yl)oxycarbonyl]carbamate

Product 1

HCID 67222637tert-butyl N-[[5-[[(2R)-2-[(2R)-4-(4-acetamidophenyl)-3-oxomorpholin-2-yl]-2-hydroxyacetyl]amino]-2-cyanophenyl]methyl]-N-[(2-methylpropan-2-yl)oxycarbonyl]carbamateYield 35.9%

Reagents, catalysts & solvents 1

HCID 86634320DMSO t-BuOHSolvent

Procedure

According to the Step 7-5 in synthetic method for EXAMPLE 7, compound 39-4 (4.3 g) and DMF were used instead of 7-4 and t-BuOH-DMSO to obtain compound 39-5 (1.46 g) as a colorless amorphous solid.

Sources & evidence

ORD record
ord-f90c7cd753b942e0919200d7b6e1c2d3
Source dataset
uspto-grants-2015_03
Patent number
US08987242B2

Reaction notes

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