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Fmoc-Gly-OH → L-Phenylalanine

HRID 1441191
Notes
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Reaction equation

HRID 1441191 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:67]([OH:69])=[O:68])[C@H:63]([CH2:65][CH3:66])[CH3:64].[NH:87](C(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O)[C@H:88]([C:99]([OH:101])=[O:100])[CH2:89][C:90]1[C:98]2[C:93](=[CH:94][CH:95]=[CH:96][CH:97]=2)[NH:92][CH:91]=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.[NH2:18][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.[NH2:87][C@H:88]([C:99]([OH:101])=[O:100])[CH2:89][C:90]1[C:98]2[C:93](=[CH:94][CH:95]=[CH:96][CH:97]=2)[NH:92][CH:91]=1.[NH2:61][C@H:62]([C:67]([OH:69])=[O:68])[C@H:63]([CH2:65][CH3:66])[CH3:64]
ParticipantsProcedureSources & evidenceReaction notes

Participants

10

Reactant 6

HCID 93124Fmoc-Gly-OHHCID 978343Fmoc-L-tryptophanHCID 978356(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)(methyl)amino)-3-phenylpropanoic acidHCID 2724629N-Fmoc-L-isoleucineHCID 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 4

HCID 6140L-PhenylalanineHCID 6305L-TryptophanHCID 6306L-IsoleucineHCID 6951135N-Methylphenylalanine

Procedure

By following essentially the procedure of Table 2 and sequentially coupling Fmoc-MePhe-OH, Fmoc-DAsp(OtBu)-OH, Fmoc-Ile-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 0.96 (1), Gly 1.04 (1), Ile 0.96 (1), MePhe 1.07 (1), Ahx 0.98 (1), Trp 0.61 (1), NH3 0.89. MS (FAB): m/e 895 (M-H)-.

Sources & evidence

ORD record
ord-52bc2b38e78540d6a794024196a29814
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