L-Aspartic Acid → HCID 12991453, compound

HRID 353592Notes

Reaction equation

C1C=[CH:3][C:4]2[N:9](O)N=[N:7][C:5]=2C=1.CN(C(ON1N=N[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[C:33]([N:40]([CH2:60][CH3:61])[CH2:41][C:42]([NH:44][C@H:45]([C:57]([OH:59])=O)[CH2:46][C:47](=[O:56])[O:48][CH2:49][C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)=[O:43])([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34].N[C@H](C(O)=O)CC(=O)[OH:66]>>[C:33]([N:40]([CH2:60][CH3:61])[CH2:41][C:42]([NH:44][C@H:45]([C:57]([NH:9][C@H:4]([C:5]([NH2:7])=[O:66])[CH2:3][CH:20]1[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]1)=[O:59])[CH2:46][C:47](=[O:56])[O:48][CH2:49][C:50]1[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=1)=[O:43])([O:35][C:36]([CH3:38])([CH3:39])[CH3:37])=[O:34]

Participants

Reactant 3

HCID 5960L-Aspartic Acid

HCID 12991452HCID 12991452, compound

HCID 86630130HCID 86630130, compound

Product 1

HCID 12991453HCID 12991453, compound

Procedure

As a specific example of the HOBT/TBTU Method, when the general procedure is followed, 10 g (24.5 mmole) of BOC-N(Et)Gly-(L)-Asp(OBzl)—OH is used, then 9.3 g of BOC-N(Et)Gly-(L)-Asp(OBzl)-(L)-Cha-NH2 is prepared (96.1 A % pure, 1.77A % diastereomer at Asp), a 67.7% theoretical yield.

Sources & evidence

ORD record: ord-d384f96e20dc42f5b16417e8184612c1
Source dataset: uspto-grants-2004_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06753409B1

Reaction notes

Loading…