Diisopropylethylamine → HCID 131729169, compound

HRID 907450Notes

Reaction equation

HRID 907450 reaction equation
CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH:25]([C:36]([O:38][CH2:39][CH:40]1[C:52]2[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=2)[C:46]2[C:41]1=[CH:42][CH:43]=[CH:44][CH:45]=2)=[O:37])[C@H:26]([C:33]([OH:35])=O)[CH2:27][O:28][C:29]([CH3:32])([CH3:31])[CH3:30].[NH2:53][C@H:54]([C:67]([O:69][CH2:70][CH:71]=[CH2:72])=[O:68])[CH2:55][C:56]1[CH:61]=[CH:60][C:59]([O:62][C:63]([CH3:66])([CH3:65])[CH3:64])=[CH:58][CH:57]=1.CCN(C(C)C)C(C)C>CN(C=O)C>[NH:25]([C:36]([O:38][CH2:39][CH:40]1[C:52]2[C:51](=[CH:50][CH:49]=[CH:48][CH:47]=2)[C:42]2[C:41]1=[CH:46][CH:45]=[CH:44][CH:43]=2)=[O:37])[C@H:26]([C:33]([NH:53][C@H:54]([C:67]([O:69][CH2:70][CH:71]=[CH2:72])=[O:68])[CH2:55][C:56]1[CH:57]=[CH:58][C:59]([O:62][C:63]([CH3:66])([CH3:65])[CH3:64])=[CH:60][CH:61]=1)=[O:35])[CH2:27][O:28][C:29]([CH3:30])([CH3:31])[CH3:32]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2724633N-(9-Fluorenylmethoxycarbonyl)-O-tert-butylserineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)2×HCID 7021133HCID 7021133, compound

Product 1

HCID 131729169HCID 131729169, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

According to the general procedure for HBTU promoted coupling, 18.26 g Fmoc-Ser(tBu), 16.95 g HBTU, 11.95 g H-Tyr(tBu)-OAllyl and 26.10 ml DIPEA were reacted in a CYTOS® Lab System in anhydrous DMF at 45° C. and at a total flow rate of 32 ml/min at residence time of 1 min to yield 26.09 g crude material (yield based on HPLC: 96%) which was used in the next step without purification.

Sources & evidence

ORD record
ord-41872591e3c84e609f9e4f162c97ea1c
Source dataset
uspto-grants-2011_09
Patent number
US08013117B2

Reaction notes

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