N-[tert-butoxycarbonyl]-L-serine → (R)-7-Amino-6,7-dihydro-9H-5-oxa-9-aza-benzocyclohepten-8-one hydrochloride

HRID 11592

Reaction equation

HRID 11592 reaction equation
C(OC(N[C@@H](C(O)=O)CO)=O)(C)(C)C.[ClH:15].[NH2:16][C@@H:17]1[C:23](=[O:24])[NH:22][C:21]2[CH:25]=[CH:26][CH:27]=[CH:28][C:20]=2[O:19][CH2:18]1.C(OC(N[C@H](C(O)=O)CO)=O)(C)(C)C>>[ClH:15].[NH2:16][C@H:17]1[C:23](=[O:24])[NH:22][C:21]2[CH:25]=[CH:26][CH:27]=[CH:28][C:20]=2[O:19][CH2:18]1

Participants

4

Reactant 3

HCID 98766N-[tert-butoxycarbonyl]-L-serineHCID 637603(R)-2-tert-butoxycarbonylamino-3-hydroxy propionic acidHCID 18599716(S)-7-Amino-6,7-dihydro-9H-5-oxa-9-aza-benzocyclohepten-8-one hydrochloride

Product 1

HCID 69195062(R)-7-Amino-6,7-dihydro-9H-5-oxa-9-aza-benzocyclohepten-8-one hydrochloride

Procedure

(R)-3-amino-2,3-dihydro-1,5-benzoxazepin-4(5H)-one hydrochloride salt was prepared from N-t-butyloxycarbonyl-D-serine by the procedures described in Itoh, et al., Chem. Pharm. Bull. 1986, 34, 1128–1147 for the preparation of (S)-3-amino-2,3-dihydro-1,5-benzoxazepin-4(5H)-one hydrochloride salt from N-t-butyloxycarbonyl-L-serine.

Sources & evidence

ORD record
ord-7c264e9779284e15bdd86025c4faf7dd
Source dataset
uspto-grants-2006_08
Patent number
US07098235B2

Linked notes

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