4-Nitrophenyl formate → HCID 131720515, compound

HRID 863257Notes

Reaction equation

[CH2:1]([NH:5][C:6](=[O:35])[C@H:7]([CH3:34])[CH2:8][C@H:9]([OH:33])[C@@H:10]([NH2:32])[CH2:11][C:12]([CH3:31])([CH3:30])[CH2:13][C:14]([N:16]1[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[O:19][CH:18]([C:26]([NH:28][CH3:29])=[O:27])[CH2:17]1)=[O:15])[CH2:2][CH2:3][CH3:4].[CH:36](OC1C=CC([N+]([O-])=O)=CC=1)=[O:37].C(NC(=O)[C@H](C)C[C@H](O)[C@@H](NC(OC(C)(C)C)=O)CC(C)(C)CC(N1C2C(=CC=CC=2)CC(NC(C)=O)C1)=O)CCC>>[CH2:1]([NH:5][C:6](=[O:35])[C@H:7]([CH3:34])[CH2:8][C@H:9]([OH:33])[C@@H:10]([NH:32][CH:36]=[O:37])[CH2:11][C:12]([CH3:30])([CH3:31])[CH2:13][C:14]([N:16]1[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[O:19][CH:18]([C:26]([NH:28][CH3:29])=[O:27])[CH2:17]1)=[O:15])[CH2:2][CH2:3][CH3:4]

Participants

Reactant 3

HCID 746284-Nitrophenyl formate

HCID 131720516HCID 131720516, compound

HCID 131720517HCID 131720517, compound

Product 1

HCID 131720515HCID 131720515, compound

Procedure

140 mg of 5(S)-amino-4(S)-hydroxy-2(R),7,7-trimethyl-8-[2(R,S)-methylaminocarbonyl-3,4-dihydro-2H-1,4-benzoxazin-4-ylcarbonyl]-octanoic acid (N-butyl)amide (Example 28)) are reacted with 100 mg of 4-nitrophenyl formate in a manner analogous to that described in Example 17): Rf (S)=0.33; FAB-M S: (M+H)+ =519.

Sources & evidence

ORD record: ord-79cbc788f4684794be8ab5521be48219
Source dataset: uspto-grants-1998_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05719141

Reaction notes

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