3-Amino-1-propanol → HCID 131731275, compound

HRID 1773110Notes

Reaction equation

HRID 1773110 reaction equation
[CH3:1][CH2:2][C@@H:3]([C@H:5]([N:36]([C:38]([C@@H:40]([NH:44][C:45]([C@@H:47]([N:51]([CH3:53])[CH3:52])[CH:48]([CH3:50])[CH3:49])=[O:46])[CH:41]([CH3:43])[CH3:42])=[O:39])[CH3:37])[C@H:6]([O:34][CH3:35])[CH2:7][C:8]([N:10]1[C@H:14]([C@H:15]([O:32][CH3:33])[C@H:16]([C:18]([NH:20][C@H:21]([C:29]([OH:31])=[O:30])[CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:19])[CH3:17])[CH2:13][CH2:12][CH2:11]1)=[O:9])[CH3:4].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C.[NH2:87][CH2:88][CH2:89][CH2:90][OH:91]>CN(C=O)C>[CH3:1][CH2:2][C@@H:3]([C@H:5]([N:36]([C:38]([C@@H:40]([NH:44][C:45]([C@@H:47]([N:51]([CH3:53])[CH3:52])[CH:48]([CH3:50])[CH3:49])=[O:46])[CH:41]([CH3:43])[CH3:42])=[O:39])[CH3:37])[C@H:6]([O:34][CH3:35])[CH2:7][C:8]([N:10]1[C@H:14]([C@H:15]([O:32][CH3:33])[C@H:16]([C:18]([NH:20][C@H:21]([C:29]([OH:31])=[O:30])[CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:19])[CH3:17])[CH2:13][CH2:12][CH2:11]1)=[O:9])[CH3:4].[OH:91][CH2:90][CH2:89][CH2:88][NH-:87]

Participants

6

Reactant 4

HCID 90863-Amino-1-propanolHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67472795Auristatin F

Product 1

HCID 131731275HCID 131731275, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
23 °C

Procedure

Auristatin F (150 mg, 0.201 mmol), HATU (153.0 mg, 0.402 mmol), and diisopropylethylamine (108 μL, 0.603 mmol) were taken up in DMF (5 mL) and 3-aminopropan-1-ol (45.9 μL, 0.603 mmol) was added. The mixture was stirred at 23° C. for 45 minutes at which time LCMS analysis showed complete disappearance of the starting material. Reduction of the volume to 1.4 mL under high vacuum followed by purification via preparative HPLC (10-90 solvent B gradient over 20 minutes eluting with 0.1% TFA/Water, 0.1% TFA/CH3CN) afforded the title compound as white solid (109 mg, 68% yield).

Workup

  1. customReduction of the volume to 1.4 mL under high vacuum followed by purification via preparative HPLC (10-90 solvent B gradient over 20 minutes eluting with 0.1% TFA/Water, 0.1% TFA/CH3CN)

Sources & evidence

ORD record
ord-f7ca4e1528c3449ca8c276832aeae23c
Source dataset
uspto-grants-2016_02
Patent number
US09254339B2

Reaction notes

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