N-(tert-butoxycarbonyl)glycine → HCID 87487937, compound

HRID 1591808Notes

Reaction equation

[CH3:1][S:2]([O-:5])(=[O:4])=[O:3].C(N(C(C)C)C(C1C=CC(OCCCCO[C:22]2[CH:23]=[CH:24][C:25]3[O:29][N:28]=[C:27]([NH:30][C:31]([C@@H:33]([NH3+:35])[CH3:34])=[O:32])[C:26]=3[CH:36]=2)=C(OC)C=1)=O)(C)C.CS(O)(=O)=O.[CH:49]([N:52]([CH:83]([CH3:85])[CH3:84])[C:53]([C:55]1[CH:80]=[CH:79][C:58]([O:59][CH2:60][CH2:61][CH2:62][CH2:63][O:64]C2C=CC3ON=C(NC([NH2+]C)=O)C=3C=2)=[C:57]([O:81][CH3:82])[CH:56]=1)=[O:54])([CH3:51])[CH3:50].C([O:90][C:91]([NH:93][CH2:94]C(O)=O)=O)(C)(C)C>>[CH3:1][S:2]([O-:5])(=[O:4])=[O:3].[CH:83]([N:52]([CH:49]([CH3:51])[CH3:50])[C:53]([C:55]1[CH:80]=[CH:79][C:58]([O:59][CH2:60][CH2:61][CH2:62][CH2:63][O:64][C:23]2[CH:22]=[CH:36][C:26]3[C:27]([NH:30][C:31]([C@@H:33]([NH:35][C:91]([NH2+:93][CH3:94])=[O:90])[CH3:34])=[O:32])=[N:28][O:29][C:25]=3[CH:24]=2)=[C:57]([O:81][CH3:82])[CH:56]=1)=[O:54])([CH3:84])[CH3:85]

Participants

Reactant 3

HCID 78288N-(tert-butoxycarbonyl)glycine

HCID 86596204HCID 86596204, compound

HCID 87487540HCID 87487540, compound

Product 1

HCID 87487937HCID 87487937, compoundYield 72%

Procedure

(1S)-1-{5-[4-(4-diisopropylcarbamoyl-2-methoxy-phenoxy)-butoxy]-benzo[d]isoxazole-3-ylcarbamoyl}-ethyl-ammonium methane sulfonic acid salt, the compound of EXAMPLE 2, was used as a starting material in place of {5-[4-(4-diisopropylcarbamoyl-2-methoxy-phenoxy)-butoxy]-benzo[d]isoxazole-3-ylcarbamoyl}-methyl-ammonium methane sulfonic acid used in the above EXAMPLE 6. According to the same method as in EXAMPLE 6, N-(t-butoxycarbonyl)glycine was used, the above title compound was obtained. (yield: 72%)

Sources & evidence

ORD record: ord-b88e1c12069d4d44b1fdf461d8984287
Source dataset: uspto-grants-2007_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07291638B2

Reaction notes

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