Dimethylformamide → {(S)-1-[(S)-2-((2S,4S)-4-Amino-2-isopropylcarbamoyl-pyrrolidin-1-yl)-1-cyclohexyl-2-oxo-ethylcarbamoyl]-ethyl}-methyl-carbamic acid tert-butyl ester

HRID 1481926Notes

Reaction equation

HRID 1481926 reaction equation
[C:1]([O:5][C:6]([N:8]([CH3:49])[C@@H:9]([CH3:48])[C:10]([NH:12][C@@H:13]([CH:42]1[CH2:47][CH2:46][CH2:45][CH2:44][CH2:43]1)[C:14](N1C[C@@H](NC(OCC2C3C=CC=CC=3C3C2=CC=CC=3)=O)C[C@H]1C(O)=O)=[O:15])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN(C(C)C)[CH:53]([CH3:55])[CH3:54].CN(C(O[N:67]1N=[N:74][C:69]2[CH:70]=[CH:71][CH:72]=[N:73][C:68]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N)(C)C.CN(C=[O:91])C>>[C:1]([O:5][C:6](=[O:7])[N:8]([C@H:9]([C:10](=[O:11])[NH:12][C@@H:13]([CH:42]1[CH2:47][CH2:46][CH2:45][CH2:44][CH2:43]1)[C:14]([N:67]1[CH2:68][C@@H:69]([NH2:74])[CH2:70][C@H:71]1[C:72](=[O:91])[NH:73][CH:53]([CH3:55])[CH3:54])=[O:15])[CH3:48])[CH3:49])([CH3:3])([CH3:2])[CH3:4]

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 6363IsopropylamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 90231415(2S,4S)-1-{(S)-2-[(S)-2-(tert-Butoxycarbonyl-methyl-amino)-propionylamino]-2-cyclohexyl-acetyl}-4-(9H-fluoren-9-ylmethoxycarbonylamino)-pyrrolidine-2-carboxylic acid2×

Product 1

HCID 90231470{(S)-1-[(S)-2-((2S,4S)-4-Amino-2-isopropylcarbamoyl-pyrrolidin-1-yl)-1-cyclohexyl-2-oxo-ethylcarbamoyl]-ethyl}-methyl-carbamic acid tert-butyl ester

Conditions

Temperature
0 °C

Procedure

To (2S,4S)-1-{(S)-2-[(S)-2-(tert-butoxycarbonyl-methyl-amino)-propionylamino]-2-cyclohexyl-acetyl}-4-(9H-fluoren-9-ylmethoxycarbonylamino)-pyrrolidine-2-carboxylic acid (Intermediate 27) (50 mg, 73.9 μmol) in DMF at 0° C. was added DIPEA (29 mg, 222 mol) and HATU (31 mg, 81.3 μmol) and the mixture was stirred at 0° C. for 15 minutes. Isopropylamine (0.10 mL) was added, the cooling bath was removed and the mixture stirred at room temperature for 1 h. The mixture was evaporated to afford the title compound which was used without purification.

Workup

  1. customthe cooling bath was removed
  2. stirringthe mixture stirred at room temperature for 1 h
  3. customThe mixture was evaporated

Sources & evidence

ORD record
ord-feba5b00fc9c40eca768e4b917ad65c3
Source dataset
uspto-grants-2016_08
Patent number
US09409888B2

Reaction notes

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