O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate → HCID 88229426, compound

HRID 382177Notes

Reaction equation

HRID 382177 reaction equation
C([O:8][C:9](=O)[CH2:10][C@@H:11](NC(OC(C)(C)C)=O)[C:12]([NH:14][C@H:15]([C:20](=[O:23])NC)[C:16]([CH3:19])([CH3:18])[CH3:17])=[O:13])C1C=CC=CC=1.CC(C)(C)[C@H](NC(=O)[C@H]([N:45]1[CH:49]=[CH:48][C:47]([C:50]2[CH:55]=[CH:54][C:53]([C:56]3[CH:61]=[CH:60][N:59]=[CH:58][CH:57]=3)=[CH:52][CH:51]=2)=[CH:46]1)CC(O)=O)CO.[O:65]([NH2:83])[Si:66]([C:79]([CH3:82])([CH3:81])[CH3:80])([C:73]1[CH:78]=[CH:77][CH:76]=[CH:75][CH:74]=1)[C:67]1[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CO.C(Cl)Cl>[O:65]([NH:83][C:9](=[O:8])[C@H:10]([N:45]1[CH:49]=[CH:48][C:47]([C:50]2[CH:55]=[CH:54][C:53]([C:56]3[CH:57]=[CH:58][N:59]=[CH:60][CH:61]=3)=[CH:52][CH:51]=2)=[CH:46]1)[CH2:11][C:12]([NH:14][C@H:15]([CH2:20][OH:23])[C:16]([CH3:18])([CH3:19])[CH3:17])=[O:13])[Si:66]([C:79]([CH3:80])([CH3:82])[CH3:81])([C:73]1[CH:74]=[CH:75][CH:76]=[CH:77][CH:78]=1)[C:67]1[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=1

Participants

6

Reactant 4

HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 11737343O-(tert-Butyldiphenylsilyl)hydroxylamineHCID 15487948N-(2,2-dimethyl-1(S)-hydroxymethyl-propyl)-3(R)-[3-[4-(pyridin-4-yl)phenyl]-1H-pyrrol-1-yl]succinamic acidHCID 537065323(R)-t-butoxycarbonylamino-N-(2,2-dimethyl-1(S)-methylcarbamoylpropyl)succinamic acid benzyl ester

Product 1

HCID 88229426HCID 88229426, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

According to the procedure described in Example 1(b) for the preparation of 3(R)-t-butyloxycarbonylamino-N-(2,2-dimethyl-1(S)-(methylcarbamoyl)propyl)succinamic acid benzyl ester, N-(2,2-dimethyl-1(S)-hydroxymethyl-propyl)-3(R)-[3-[4-(pyridin-4-yl)phenyl]-1H-pyrrol-1-yl]succinamic acid (prepared as described in Example 5(a)) and t-butyldiphenylsiloxyamine were coupled with TBTU. Flash column chromatography with 0-5% MeOH/CH2Cl2 gradient eluant furnished in 43% yield N1-t-butyldiphenylsiloxy-N4-[2,2-Dimethyl-1(S)-(hydroxymethyl)propyl]-2(R)-[3-[4-(pyridin-4-yl)phenyl]-1H-pyrrol-1-yl]succinamide as an amorphous solid.

Sources & evidence

ORD record
ord-f1b87d184ed1493fb304717ef7e469d1
Source dataset
uspto-grants-2001_10
Patent number
US06306892B1

Reaction notes

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