Diisopropylcarbodiimide → HCID 131731276, compound

HRID 2405552Notes

Reaction equation

HRID 2405552 reaction equation
[C:1]([NH:8][C@H:9]([C:11]([OH:13])=[O:12])[CH3:10])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(N=C=NC(C)C)(C)C.[CH3:23][CH2:24][C@@H:25]([C@H:27]([N:58]([C:60]([C@@H:62]([NH:66][C:67]([C@@H:69]([N:73]([CH3:75])[CH3:74])[CH:70]([CH3:72])[CH3:71])=[O:68])[CH:63]([CH3:65])[CH3:64])=[O:61])[CH3:59])[C@H:28]([O:56][CH3:57])[CH2:29][C:30]([N:32]1[C@H:36]([C@H:37]([O:54][CH3:55])[C@H:38]([C:40]([NH:42][C@H:43]([C:51]([OH:53])=[O:52])[CH2:44][C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)=[O:41])[CH3:39])[CH2:35][CH2:34][CH2:33]1)=[O:31])[CH3:26].[OH:76][CH2:77][CH2:78][CH2:79][NH-:80]>CN(C1C=CN=CC=1)C.ClCCl>[CH3:23][CH2:24][C@@H:25]([C@H:27]([N:58]([C:60]([C@@H:62]([NH:66][C:67]([C@@H:69]([N:73]([CH3:75])[CH3:74])[CH:70]([CH3:72])[CH3:71])=[O:68])[CH:63]([CH3:65])[CH3:64])=[O:61])[CH3:59])[C@H:28]([O:56][CH3:57])[CH2:29][C:30]([N:32]1[C@H:36]([C@H:37]([O:54][CH3:55])[C@H:38]([C:40]([NH:42][C@H:43]([C:51]([OH:53])=[O:52])[CH2:44][C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)=[O:41])[CH3:39])[CH2:35][CH2:34][CH2:33]1)=[O:31])[CH3:26].[C:1]([NH:8][C@H:9]([C:11]([OH:13])=[O:12])[CH3:10])([O:3][C:4]([CH3:7])([CH3:5])[CH3:6])=[O:2].[OH:76][CH2:77][CH2:78][CH2:79][NH-:80]

Participants

6

Reactant 3

HCID 12734DiisopropylcarbodiimideHCID 85082Tert-butoxycarbonylalanineHCID 131731275HCID 131731275, compound

Product 1

HCID 131731276HCID 131731276, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

BOC-L-alanine (117.0 mg, 0.618 mmol) and DMAP (94.0 mg, 0.772 mmol) were taken up in dichloromethane and then diisopropylcarbodiimide (52.6 μL, 0.340 mmol) was added. The reaction mixture was cooled to 0° C. and stirred for 10 minutes after which auristatin F-hydroxypropylamide (124 mg, 0.154 mmol, prepared as described in Example 48) was added. The reaction mixture was warmed to 23° C. and stirred for 18 hours. Purification via preparative HPLC followed by removal of the water via lyophilization afforded the title compound as beige solid (112 mg, 75% yield).

Workup

  1. additionwas added
  2. temperatureThe reaction mixture was warmed to 23° C.
  3. customPurification via preparative HPLC
  4. customfollowed by removal of the water via lyophilization

Sources & evidence

ORD record
ord-1de9dccca7ed43b48269df2328cee150
Source dataset
uspto-grants-2014_08
Patent number
US08808679B2

Reaction notes

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