HCID 86647447, compound → HCID 59569986, compound

HRID 2071188Notes

Reaction equation

N[C@@H](CC1C=CC=CC=1)[C@H](O)CN(CC1C=C(N(C)S(C)(=O)=O)C=C(C(C)C)C=1)C(=O)OC(C)(C)C.[C:37]([NH:40][C:41]1[CH:42]=[C:43]([CH:65]=[C:66]([C:68]([CH3:70])=[CH2:69])[CH:67]=1)[CH2:44][NH:45][CH2:46][C@@H:47]([OH:64])[C@@H:48]([NH:56][C:57](=[O:63])[O:58][C:59]([CH3:62])([CH3:61])[CH3:60])[CH2:49][C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)(=[O:39])[CH3:38]>>[C:37]([NH:40][C:41]1[CH:42]=[C:43]([CH:65]=[C:66]([CH:68]([CH3:70])[CH3:69])[CH:67]=1)[CH2:44][NH:45][CH2:46][C@@H:47]([OH:64])[C@@H:48]([NH:56][C:57](=[O:63])[O:58][C:59]([CH3:62])([CH3:61])[CH3:60])[CH2:49][C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)(=[O:39])[CH3:38]

Participants

Reactant 2

HCID 86647447HCID 86647447, compound

HCID 86647448HCID 86647448, compound

Product 1

HCID 59569986HCID 59569986, compound

Procedure

tert-butyl (2S,3R)-4-(3-acetamido-5-isopropylbenzylamino)-3-hydroxy-1-phenylbutan-2-ylcarbamate was synthesized in a similar manner to Boc-protected tert-butyl (2R,3S)-3-amino-2-hydroxy-4-phenylbutyl(3-isopropyl-5-(N-methylmethylsulfonamido)benzyl)carbamate by reducing tert-butyl (2S,3R)-4-(3-acetamido-5-(prop-1-en-2-yl)benzylamino)-3-hydroxy-1-phenylbutan-2-ylcarbamate.

Sources & evidence

ORD record: ord-a9c52682852e42c1af8ce907d5b05f86
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08299267B2

Reaction notes

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