4-Nitrophenol → L-Serine

HRID 1108050Notes

Reaction equation

HRID 1108050 reaction equation
C([O:8][C:9]1C=CC=C[C:10]=1[C:11]([OH:13])=[O:12])C1C=CC=CC=1.C1C([N+:24]([O-])=O)=CC=C(O)C=1.C1(N=C=NC2CCCCC2)CCCCC1.[N+:43]([C:46]1[CH:51]=[CH:50][C:49]([C:52]2[C:53]([O:61][CH2:62][C:63]3[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=3)=[C:54]([CH:58]=[CH:59][CH:60]=2)[C:55]([O-:57])=[O:56])=[CH:48][CH:47]=1)([O-:45])=[O:44]>C(OCC)(=O)C.O1CCCC1.C(N(CC)CC)C>[N+:43]([C:46]1[CH:51]=[CH:50][C:49]([C:52]2[C:53]([O:61][CH2:62][C:63]3[CH:64]=[CH:65][CH:66]=[CH:67][CH:68]=3)=[C:54]([CH:58]=[CH:59][CH:60]=2)[C:55]([O-:57])=[O:56])=[CH:48][CH:47]=1)([O-:45])=[O:44].[NH2:24][C@H:10]([C:11]([OH:13])=[O:12])[CH2:9][OH:8]

Participants

9

Reactant 4

HCID 9804-NitrophenolHCID 10868DicyclohexylcarbodiimideHCID 18105812-Benzyloxybenzoic acidHCID 70183929HCID 70183929, compound

Product 2

HCID 5951L-SerineHCID 70183929HCID 70183929, compound

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Benzyloxybenzoic acid 4 was then reacted with p-nitrophenol 5 and dicyclohexylcarbodiimide (DCC) in ethyl acetate to produce, after work-up, 4-nitrophenyl-2-(benzyloxy)benzoate 6 in 45% yield. Treatment of the benzoate 6 with L-serine 7 and triethylamine (TEA) in tetrahydrofuran (THF)/water gave the protected E/D fragment 8 of Exochelin 786SM(R) in 79% yield. This segment undergoes subsequent reaction with a protected form of the C/F fragment to generate the largest subunit of the target compound.

Workup

  1. customto produce

Sources & evidence

ORD record
ord-121f05e5bbac4a90811d122c447d41ea
Source dataset
uspto-grants-2000_05
Patent number
US06063919

Reaction notes

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