N-(tert-butoxycarbonyl)glycine → N-Boc-glycyl-L-proline benzyl ester

HRID 716524Notes

Reaction equation

HRID 716524 reaction equation
C(NCC(O)=O)(OC(C)(C)C)=O.Cl.C(OC(=O)[C@@H]1CCCN1)C1C=CC=CC=1.[CH2:29]([O:36][C:37]([C@@H:39]1[CH2:43][CH2:42][CH2:41][N:40]1[C:44](=[O:60])[C@H:45]([NH:52][C:53]([O:55][C:56]([CH3:59])([CH3:58])[CH3:57])=[O:54])C1C=CC=CC=1)=[O:38])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>>[CH2:29]([O:36][C:37]([C@@H:39]1[CH2:43][CH2:42][CH2:41][N:40]1[C:44](=[O:60])[CH2:45][NH:52][C:53]([O:55][C:56]([CH3:58])([CH3:57])[CH3:59])=[O:54])=[O:38])[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

4

Reactant 3

HCID 78288N-(tert-butoxycarbonyl)glycineHCID 2733413Proline benzyl ester hydrochlorideHCID 15288611(S,R)-1-(2-tert-butoxycarbonylamino-2-phenylacetyl)-pyrrolidine-2-carboxylic acid benzyl ester

Product 1

HCID 13152016N-Boc-glycyl-L-proline benzyl ester

Procedure

Compound 26 was synthesized from N-Boc-glycine and L-proline benzyl ester hydrochloride, following the procedure as described for compound 2a, as a white crystallized solid. MS (ESI, EI+) m/z=363 (MH+).

Workup

  1. customas a white crystallized solid

Sources & evidence

ORD record
ord-041d1bc54f624b73875af38c6f667297
Source dataset
uspto-grants-2015_11
Patent number
US09187496B2

Reaction notes

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