Fmoc-Gly-OH → L-Phenylalanine

HRID 1441193

Reaction equation

HRID 1441193 reaction equation
[C:1]([N:18](C)[C@H:19]([C:27]([OH:29])=[O:28])[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O.C(N(C)[C@H](C(O)=O)CC(=O)OC(C)(C)C)(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O.[NH:62](C(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O)[C@H:63]([C:68]([OH:70])=[O:69])[CH2:64][CH2:65][CH2:66][CH3:67].[NH:88](C(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O)[C@H:89]([C:100]([OH:102])=[O:101])[CH2:90][C:91]1[C:99]2[C:94](=[CH:95][CH:96]=[CH:97][CH:98]=2)[NH:93][CH:92]=1.N(C(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O)CC(O)=O>>[NH2:18][C@H:19]([C:27]([OH:29])=[O:28])[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[NH:18]([CH3:1])[C@H:19]([C:27]([OH:29])=[O:28])[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[NH2:62][C@H:63]([C:68]([OH:70])=[O:69])[CH2:64][CH2:65][CH2:66][CH3:67].[NH2:88][C@H:89]([C:100]([OH:102])=[O:101])[CH2:90][C:91]1[C:99]2[C:94](=[CH:95][CH:96]=[CH:97][CH:98]=2)[NH:93][CH:92]=1

Participants

9

Reactant 5

HCID 93124Fmoc-Gly-OHHCID 978343Fmoc-L-tryptophanHCID 978356(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-phenylpropanoic acidHCID 7009636(2S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)hexanoic acid2×HCID 7019716N-alpha-(9-Fluorenylmethyloxycarbonyl)-N-alpha-methyl-L-aspartic acid beta-t-butyl ester

Product 4

HCID 6140L-PhenylalanineHCID 6305L-TryptophanHCID 21236CaprineHCID 6951135N-Methylphenylalanine

Procedure

By following essentially the procedure of Table 2 and sequentially coupling Fmoc-MePhe-OH, Fmoc-MeAsp(OtBu)-OH, Fmoc-Ahx-OH, Fmoc-Trp-OH, Fmoc-Gly-OH, Fmoc-Ahx-OH and Hpa-OSu, the title compound was prepared. Amino Acid analysis following acid decomposition gave MeAsp 1.01 (1), Gly 1.05 (1), MePhe 0.91 (1), Ahx 2.02 (2), Trp 0.84 (1), NH3 0.82. MS (FAB): m/e 909 (M-H)-.

Sources & evidence

ORD record
ord-0e70947c102c424092ae9d4f378d191a
Source dataset
uspto-grants-1996_03
Patent number
US05502164

Linked notes

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