4-Methylmorpholine → 4-tert-Butyl hydrogen N-((phenylmethoxy)carbonyl)-L-aspartate

HRID 327504

Reaction equation

HRID 327504 reaction equation
CN(C(ON1N=N[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN1CC[O:29]CC1.C1C=CC([CH2:38][O:39][C:40](NCCC(O)=O)=[O:41])=CC=1.[NH2:48][C@H:49]([C:58]([NH:60][C@H:61]([C:69]([O:71][C:72]([CH3:75])([CH3:74])[CH3:73])=[O:70])[CH2:62][C:63]1[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=1)=[O:59])[CH2:50][C:51](=[O:57])[O:52][C:53]([CH3:56])([CH3:55])[CH3:54]>>[NH:48]([C:40]([O:39][CH2:38][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)=[O:41])[C@H:49]([C:58]([OH:59])=[O:29])[CH2:50][C:51](=[O:57])[O:52][C:53]([CH3:54])([CH3:55])[CH3:56].[NH2:60][C@H:61]([C:69]([O:71][C:72]([CH3:75])([CH3:74])[CH3:73])=[O:70])[CH2:62][C:63]1[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=1

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 75313N-Benzyloxycarbonyl-beta-alanineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 12968763HCID 12968763, compound

Product 2

HCID 1110824-tert-Butyl hydrogen N-((phenylmethoxy)carbonyl)-L-aspartateHCID 6931633tert-butyl (2S)-2-amino-3-phenylpropanoate

Procedure

834 mg of HBTU and 0.24 ml of N-methylmorpholine were added at 0° C. under argon to a solution of 446 mg of Z-β-Al-a-OH and 785 mg of H-Asp(O-tBu)-Phe-O-tBu (obtained from the condensation of Z-Asp(O-tBu)-OH with H-Phe-O-tBu followed by hydrogenolysis). After 5 hours, the mixture was concentrated and the residue was partitioned in ethyl acetate/5% NaHCO3. The organic phase was washed with water and 1M KHSO4. The organic extracts were dried, filtered and concentrated. The residue was recrystallised from ethyl acetate/diisopropyl ether resulting in 592 mg of Z-β-Ala-Asp(O-tBu)-Phe-O-tBu, m.p. 138°-139° C.

Sources & evidence

ORD record
ord-83753e6947ab4843bcc0f19dd8d8f05d
Source dataset
uspto-grants-1993_12
Patent number
US05273982

Linked notes

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