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Fmoc-Gly-OH → L-Phenylalanine

HRID 1441192
Notes
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Reaction equation

HRID 1441192 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.N(C(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O)[C@@H](C(O)=O)CC(=O)OC(C)(C)C.[NH:61](C(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O)[C@H:62]([C:70]([OH:72])=[O:71])[CH2:63][C:64]1[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=1.[NH:90](C(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O)[C@H:91]([C:102]([OH:104])=[O:103])[CH2:92][C:93]1[C:101]2[C:96](=[CH:97][CH:98]=[CH:99][CH:100]=2)[NH:95][CH:94]=1.N(C(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O)CC(O)=O.N(C(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O)[C@H](C(O)=O)CCCC>>[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.[NH2:61][C@H:62]([C:70]([OH:72])=[O:71])[CH2:63][C:64]1[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=1.[NH2:90][C@H:91]([C:102]([OH:104])=[O:103])[CH2:92][C:93]1[C:101]2[C:96](=[CH:97][CH:98]=[CH:99][CH:100]=2)[NH:95][CH:94]=1
ParticipantsProcedureSources & evidenceReaction notes

Participants

9

Reactant 6

HCID 93124Fmoc-Gly-OHHCID 978331Fmoc-phenylalanineHCID 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 acid
HCID 7018816
4-tert-Butyl N-((9H-Fluoren-9-ylmethoxy)carbonyl)-D-aspartate

Product 3

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

Procedure

By following essentially the procedure of Table 2 and sequentially coupling Fmoc-MePhe-OH, Fmoc-DAsp(OtBu)-OH, Fmoc-Phe-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 Asp 1.01 (1), Gly 0.99 (1), MePhe 1.06 (1), Ahx 1.02 (1), Trp 1.06 (1), Phe 0.94 (1), NH3 0.82. MS (FAB): m/e 931 (M-H)-.

Sources & evidence

ORD record
ord-cb08aa5f47424d19ac33ed09291c68ca
Source dataset
uspto-grants-1996_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05502164

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes