Acetic Anhydride → HCID 131722627, compound

HRID 1066711Notes

Reaction equation

HRID 1066711 reaction equation
N(C(OC(C)(C)C)=O)[C@H](C(O)=O)CC1C=C[C:7]([O:10]P(OCC)(OCC)=O)=[CH:6]C=1.[NH2:29][C@H:30]([C:47]([NH:49][C@H:50]([C:54]([NH:56][C@H:57]([C:62]([NH:64][C@H:65]([C:69]([NH2:71])=[O:70])[CH:66]([CH3:68])[CH3:67])=[O:63])[CH2:58][C:59](=[O:61])[NH2:60])=[O:55])[CH:51]([CH3:53])[CH3:52])=[O:48])[CH2:31][C:32]1[CH:37]=[CH:36][C:35]([O:38][P:39]([O:44][CH2:45][CH3:46])([O:41][CH2:42][CH3:43])=[O:40])=[CH:34][CH:33]=1.CCN(C(C)C)C(C)C.C(OC(=O)C)(=O)C>CN(C=O)C>[NH:29]([C:7]([CH3:6])=[O:10])[C@H:30]([C:47]([NH:49][C@H:50]([C:54]([NH:56][C@H:57]([C:62]([NH:64][C@H:65]([C:69]([NH2:71])=[O:70])[CH:66]([CH3:68])[CH3:67])=[O:63])[CH2:58][C:59](=[O:61])[NH2:60])=[O:55])[CH:51]([CH3:52])[CH3:53])=[O:48])[CH2:31][C:32]1[CH:33]=[CH:34][C:35]([O:38][P:39]([O:44][CH2:45][CH3:46])([O:41][CH2:42][CH3:43])=[O:40])=[CH:36][CH:37]=1

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 81531DiisopropylethylamineHCID 10070574HCID 10070574, compoundHCID 131722628HCID 131722628, compound

Product 1

HCID 131722627HCID 131722627, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was obtained by analogous manner as described in Example 18, but using BocTyr(PO3Et2)OH. The N-acetylation was performed by treatment of crude H—Tyr(PO3Et2)—Val—Asn—Val—NH2 with 1.5 equiv. of DIEA and 5 equiv. of acetic anhydride in DMF for 2 h at 25° C. The final compound was obtained with chromatographic purity (HPLC) of 90.0%. Amino acid ratios: Val 2 (2); Asx 1.17 (1); Tyr 0.87 (1). Peptide content: 83%. FAB mass spectroscopy; m/z 671 [M—H]+. (MW 670.1)

Sources & evidence

ORD record
ord-5353513a0c4f42509da40dcf791777d5
Source dataset
uspto-grants-2001_06
Patent number
US06245742B1

Reaction notes

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